170.Synthesis towards Phainanoid F: Photo-induced 6π- Electrocyclization for Constructing Contiguous All-Carbon Quaternary Centers

Hao-Yuan Liu, Zhen-Yu Zhang, Yi-Ke Zhou, Jia-Hua Chen, Zhen Yang,* and Yuan-He Li* Chem Asian J.2023,18, e20230062 In this paper, we report an efficient strategy for synthesizing the DEFGH rings of phainanoid F. The key to the construction of the 13,30-cyclodammarane skeleton of the molecule was a photo-induced 6π-electrocyclization and a homoallylic elimination. Notably, this is a rare example of using electrocyclization reaction to simultaneously construct two vicinal quaternary carbons in total synthesis. The strategy outlined here forms the basis of our total synthesis of Phainanoid F,...

read more

169.Regioselective Hydroxylation of Flavonoids by Transition-Metal-Catalyzed C−H Bond Oxidation

Shu-Min Lu, Chao Chen, Chang Liu, Rudong Liu, Jia-Hua Chen,* Zhongchao Zhang,* and Zhen Yang* Org. Lett. 2023, 25(13), 2264–2269 Regioselective synthesis of 5,6,7-trihydroxyl and 5,7,8-trihydroxyl flavones has been achieved via a transition-metal-catalyzed C–H oxidation as the key step using naturally enriched 5,7-dihydroxyl flavone. The developed chemistry was applied to the synthesis of the naturally occurring and biologically active flavonoids wogonin (2), oroxylin A (3), and their glycosylated derivatives (4 and 5) as potential carnitine palmitoyltransferase 1...

read more

168.Highly Stereoselective Diels-Alder Reactions Catalyzed by Diboronate Complexes

Yuan-He Li, Su-Lei Zhang, Yong Lu, Bo Xiao, Tian-Yu Sun, Qian-Qian Xu, Jia-Hua Chen,* Zhen Yang* Angew. Chem. Int. Ed. 2023, 62(33) A highly enantioselective catalytic system for exo-Diels–Alder reactions was developed based on the newly discovered bispyrrolidine diboronates (BPDBs). When activated various Lewis or Brønsted acids, BPDBs could catalyze highly stereoselective asymmetric exo-Diels–Alder reactions of monocarbonyl-based dienophiles. When 1,2-dicarbonyl-based dienophiles are used, the catalyst can sterically distinguish between the two binding sites, which leads to highly...

read more

167.Synthesis of the 5/6 fused-spiro tricyclic framework of manginoid A

Zhiming Yan, Chunbo Zhao, Zhen Yang*, Jianxian Gong* Tetrahedron Letters 2023, 117 (2023), 154361-154363 We developed a concise, ten-step route to the 5/6 fused-spiro tricyclic framework (A/B/C rings) of manginoid A from the starting materials cyclopentenone and 1,3-cyclohexanedione. Michael addition and subsequent Mukaiyama aldol reaction introduced two side chains at the α,β-positions of cyclopentenone. Tsuji–Trost allylation of this cyclopentenone moiety and 1,3-cyclohexanedione afforded a key intermediate. A late-stage Michael addition formed the spiro-fused tricyclic...

read more

袁泓毅%1169452375@qq.com%Sichuan University

B.S. (2018-2022) : Sichuan University. Advisor: Prof.Liu Bo Ph.D. (2022-now) : School of Chemical Biology & Biotechnology, Shenzhen Graduate School, Peking University. Advisor: Prof.Zhen Yang

read more

宋治霖%zl_song@stu.pku.edu.cn%Xiamen University

Education B.S. (2017-2021): College of Chemistry and Chemical Engineering, Xiamen University (Advior:  Prof. Su-Yuan Xie, Prof. Jun Zhu) PhD. (2021-now) : School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University. Advisor: Prof. Zhen Yang, Prof. Jianxian Gong and Prof. Jun Huang. Research Interest Investigate the Reaction Mechanisms in Organic Chemistry via DFT (Density Functional Theory), Natural Product...

read more

166.Recent advances in total synthesis of natrual products containing contiguous all carbon quaternary stereocenters

Zhongchao Zhang, Zhen Yang * SCIENTIA SINICA Chimica 2023, 53(3), 277-288 Contiguous all carbon quaternary stereocenters are common structural units in bioactive natural products with significant synthetic challenges. In this paper, we reviewed our recent progresses in total synthesis of complex natural products containing contiguous all carbon quaternary stereocenters firstly. Then, four different synthetic strategies concerning the construction of contiguous all carbon quaternary stereocenters (≥3) were summarized. Finally, the total synthesis of waihoensene and crinipellins reported by...

read more

165.Identification and semisynthesis of (−)-anisomelic acid as oral agent against SARS-CoV-2 in mice

Hai-Xin Yu, Nan Zheng, Chi-Tai Yeh, Chien-Ming Lee, Qi Zhang, Wen-Lv Zheng, Qing Chang, Yuan-He Li, Yu-Jun Li, Gui-Zhen Wu∗, Jun-Min Quan∗, Lin-Qi Zhang∗, Yew-Min Tzeng∗ and Zhen Yang∗ National Science Review 2022, 9(11), nwac 176 (−)-Anisomelic acid, isolated from Anisomeles indica (L.) Kuntze (Labiatae) leaves, is a macrocyclic cembranolide with a trans-fused α-methylene-γ-lactone motif. Anisomelic acid effectively inhibits SARS-CoV-2 replication and viral-induced cytopathic effects with an EC50 of 1.1 and 4.3 μM, respectively. Challenge studies of SARS-CoV-2-infected...

read more

164.Electrocatalytic Isomerization of Allylic Alcohols: Straightforward Preparation of β-Aryl-Ketones

Anding Li, Nan Zheng, Kai Guo, Zhongchao Zhang and Zhen Yang* Catalysts 2022, 12(3), 333 Electrochemical synthesis has been rapidly developing over the past few years. Here, we report a practical and eco-friendly electrocatalytic isomerization of allylic alcohols to their corresponding carbonyl compounds. This reaction can be carried out in undivided cells without the addition of external chemical oxidants and metal catalysts. Moreover, this reaction features a broad substrate scope including challenging allylic alcohols bearing tri- and tetra-substituted olefins and affords straightforward...

read more

163.Semisynthesis of (−)-Bufospirostenin A Enabled by Photosantonin Rearrangement Reaction

Jun Huang,* Tingting Cao, Zhongchao Zhang, and Zhen Yang* J. Am. Chem. Soc. 2022, 144,(6), 2479–2483 An enantioselective semisynthesis of (−)-bufospirostenin A is described. The key steps in the synthesis involve use of our proposed biomimetic and diastereoselective photosantonin rearrangement reaction for construction of the 5/7 bicyclic motif, and a Co-catalyzed reversible double-bond isomerization reaction for installing the double bond in the seven-membered...

read more

162.Palladium-Catalyzed Intramolecular Diarylation of 1,3-Diketone in Total Synthesis of (±)-Spiroaxillarone A

Tingting Cao, Lei Zhu,* Jun Huang,* and Zhen Yang* Org. Lett. 2022, 24,(7), 1491–1495 A sterically congested all-carbon quaternary center was installed for the first time via a Pd-catalyzed cascade diarylation with aryl bromides and acyclic 1,3-diketones. This method was used as a key step in the total synthesis of (±)-spiroaxillarone A. Computational experimental results indicated that the selective diarylation is accelerated by the higher free-energy barriers of the endothermic transmetalation and reductive elimination in the first arylation...

read more

161.Concise Synthesis of 7-Deoxypsammaplysins K and O and 7-Deoxyceratinamide A by 1,3-Dipole Cycloaddition

Lijie Zhang, Rongya Wang, Chao Wang, Bingyan Liu, Jinfeng Yang, Zhongchao Zhang, Jun Huang,*and Zhen Yang* Org. Lett. 2022, 24(21), 3786–3791 A spiro-oxepin isoxazoline skeleton was constructed via 1,3-dipole cycloaddition as a key step, which enabled the total syntheses of 7-deoxyceratinamide A and 7-deoxypsammaplysins K and O. The developed chemistry could be applied to total synthesis of structurally diverse spiro-oxepin isoxazoline-based marine natural...

read more

160.Total Syntheses of Vicinal Dichloride Monoterpenes Enabled by AzaBellus−̌ Claisen Rearrangement

Jiangqun Cheng, Yuan-He Li, Jun Huang,* and Zhen Yang* Org. Lett. 2021, 23(21), 8465–8470 Diastereoselective syntheses of syn– and anti-vicinal dihalides were achieved via an aza-Belluš–Claisen rearrangement, which involved the reaction of an α-chloro carboxylic acid chloride with halogen-substituted trans-allyl morpholines in the presence of Lewis acids. The developed method was used for the total synthesis of a group of monoterpene natural products bearing vicinal dichloride...

read more

159.Total Synthesis of (+)-Cyclobutastellettolide B

Zhongchao Zhang, Sijia Chen, Fu Tang, Kai Guo, Xin-Ting Liang, Jun Huang,* and Zhen Yang* J. Am. Chem. Soc. 2021, 143,(43), 18287–18293 A convenient enantioselective total synthesis of (+)-cyclobutastellettolide B via a strategy that involves a diastereoselective Johnson–Claisen rearrangement, a regioselective cyclopropoxytrimethylsilane ring-opening reaction, and a Norrish–Yang cyclization is described. The results of computational and experimental studies indicate that the regio- and stereoselectivity of the Norrish–Yang reaction are controlled by the C–H bond dissociation energy...

read more

158.A Synthetic Route to The Core Structure of (−)-Retigeranic Acid A

Xiao Wang, Dian Li, Junlin Zhang, Jianxian Gong, Junkai Fu,* and Zhen Yang* Org. Lett. 2021, 23,(13), 5092–5097 Retigeranic acid A is a uniquely structured pentacyclic sesterterpene bearing eight stereogenic centers. We report a concise route to the core structure of (−)-retigeranic acid A. The stereochemistry of its six chiral centers and three quaternary carbon centers was well-controlled. This route features two intramolecular Pauson–Khand reactions (IMPKRs): the first forged the D and E rings to deliver the triquinane subunit, and the second constructed the A and B rings and...

read more

157.Stereoselective Synthesis of (±)-Cephanolide B

Anding Li, Ziru He, Bingyan Liu, Zhen Yang*, and Zichun Zhang* Org. Lett. 2021, 23,(23), 9237–9240 A concise and stereoselective total synthesis of (±)-cephanolide B was achieved in 15 steps. The key steps in the synthesis were as follows: (i) an intermolecular Diels–Alder reaction followed by lactonization to form the oxabicyclo[2.2.2]octane DE ring; (ii) a tandem reaction, featuring an intramolecular Pauson–Khand reaction, a 6π-electrocyclization, and an oxidative aromatization by O2, to construct the ABC-tricyclic rings (6-5-6); and (iii) a phthaloyl peroxide-mediated arene...

read more

156.Synthetic Strategy for Construction of Highly Congested Tetracyclic Core (6–5–7–4) of Harziane Diterpenoids

Qian Tu, Zheyuan Wang, Zhongchao Zhang, Jun Huang*, and Zhen Yang* Org. Lett. 2021, 23(11), 4088–4093 The structurally intriguing tetracyclic core of complex harziane diterpenoid was constructed in 14 steps from commercially available 3-ethoxycyclohex-2-en-1-one. The key steps were a Mn/Cu-mediated oxidative 1,3-dicarbonyl radical cascade cyclization reaction, which diastereoselectively formed the core of dimethylbicyclo[3.2.1]octane structure, and a Au-catalyzed diastereoselective formal [2 + 2] cycloaddition for construction of the harziane diterpenoid tetracyclic framework. The...

read more

155.Stereoselective Synthesis of trans-Decalin-Based Spirocarbocycles via Photocyclization of 1,2-Diketones

Sijia Chen, Zhongchao Zhang, Chongguo Jiang, Chunbo Zhao, Haojie Luo, Jun Huang*, and Zhen Yang* ACS Omega 2021, 6(29), 18848–18859 Diastereoselective synthesis of the trans-decalin-based α-hydroxyl butanone spirocarbocycles bearing all-carbon quaternary stereogenic centers has been achieved via Norrish–Yang photocyclization of trans-decalin-substituted-2,3-butanediones using daylight. Density functional theory (DFT) calculations suggest that this diastereoselective reaction is affected by both substrate conformation and intramolecular hydrogen bonds. The developed chemistry could be...

read more

154.Synthesis of Desacyl Furanmonogones A and B

Dian Li, Jinfeng Yang, Bingyan Liu, Jianxian Gong,* and Zhen Yang* Org. Lett. 2021, 23(12), 4532–4537 A strategy for the stereoselective synthesis of desacyl furanmonogones A and B has been achieved. The key steps in this synthesis are (1) an Fe(ClO4)3-mediated oxidative radical cyclization for construction of a cis-fused [5–6]-bicyclic core with a bridged lactone substitute, (2) a phosphorane-mediated rearrangement to convert the cis-fused [5–6]-bicyclic core to the corresponding trans-fused [5–6]-bicyclic core, and (3) a Au-catalyzed cascade reaction for formation of the...

read more

153.Stereoselective Synthesis of Cyclohepta[b]indoles via Visible‐Light‐Induced [2+2]‐Cycloaddition/retro‐Mannich‐type Reactions

Xin-Peng Mu, Yuan-He Li, Nan Zheng, Jian-Yu Long, Si-Jia Chen, Bing-Yan Liu, Chun-Bo Zhao, and Zhen Yang* Angew.Chem. Int. Ed. 2021, 60(20), 11211-11216 A novel method for the concise synthesis of cyclohepta[ b ]indoles in high yields was developed. The method involves a visible‐light‐induced, photocatalyzed [2+2]‐cycloaddition / retro‐Mannich‐type reaction of enaminones. Experimental and computational studies suggested that the reaction is a photoredox process initiated by single‐electron oxidation of an enaminone moiety, which undergoes subsequent cyclobutane formation and...

read more

152.Navigating the Pauson–Khand Reaction in Total Syntheses of Complex Natural Products

Zhen Yang* Acc. Chem. Res. 2021, 54(3), 556–568 “Total synthesis endeavors provide wonderful opportunities to discover and invent new synthetic reactions as a means to advance organic synthesis in general. Such discoveries and inventions can occur when the practitioner faces intransigent problems that cannot be solved by known methods and/or when method improvements are desired in terms of elegance, efficiency, cost-effectiveness, practicality, or environmental friendliness” (K. C. Nicolaou et al. from their review in CCS Chem.2019, 1, 3–37). To date tens of thousands of bioactive...

read more

151.Asymmetric Total Synthesis of (−)-Spirochensilide A, Part 2: The Final Phase and Completion

Xin-Ting Liang, Bao-Chuan Sun, Nan Zhang, Zhong-Chao Zhang, Yuan-He Li, Qian-Qian Xu, Chang Liu, Jia-Hua Chen,* and Zhen Yang* J. Org. Chem. 2021, 86(3), 2158–2172 The final phase of the total synthesis of (−)-spirochensilide A is described. A tungsten-mediated cyclopropene-based Pauson–Khand reaction was developed to form the spiral CD ring system with desired stereochemistry at the C13 quaternary center. Other important steps enabling completion of this synthesis included an intermolecular aldol condensation to link the ABCD core with the EF fragment and a Cu-mediated 1,4-addition to...

read more

150.Asymmetric Total Synthesis of (−)-Spirochensilide A, Part 1: Diastereoselective Synthesis of the ABCD Ring and Stereoselective Total Synthesis of 13(R)-Demethyl Spirochensilide A

Xin-Ting Liang, Bao-Chuan Sun, Chang Liu, Yuan-He Li, Nan Zhang, Qian-Qian Xu, Zhong-Chao Zhang, Yi-Xin Han, Jia-Hua Chen,* and Zhen Yang* J. Org. Chem. 2021, 86(3), 2135–2157 A concise and diastereoselective construction of the ABCD ring system of spirochensilide A is described. The key steps of this synthesis are a semipinacol rearrangement reaction to stereoselectively construct the AB ring system bearing two vicinal quaternary chiral centers and a Co-mediated Pauson–Khand reaction to form the spiro-based bicyclic CD ring system. This chemistry leads to the stereoselective synthesis...

read more

149.Synthetic Study Toward the 4,5-Spirocycle Skeleton of Phainanoids

Jiang, Chongguo†, Chen, Sijia†, Gong, Jianxian*, Yang, Zhen* Acta Chim. Sinica 2020, 78(9), 928—932 Attempts to synthesize the 4,5-spirocycle skeleton of Phainanoids by rhodium-catalyzed arylative cyclization of alkynone 5 and the addition of Grignard reagent 9 to α-alkoxyl cyclobutone 8, followed by intramolecular SNAr reaction are reported. Phainanoids, highly modified triterpenoids, were isolated from Phyllanthus hainanensis by Yue and co-workers. They have been found to show intriguing immunosuppressive activities. The most potent of them, Phainanoid F, inhibit the proliferation...

read more

148.Total Synthesis of (+)-Haperforin G

Wei Zhang, Zhenyu Zhang, Jun-Chen Tang, Jin-Teng Che, Hao-Yu Zhang, Jia-Hua Chen,* and Zhen Yang* J. Am. Chem. Soc. 2020, 142(46), 19487–19492 A concise chemical synthesis of (+)-haperforin G in 20 steps from commercially available starting materials is achieved with the integration of the Co-catalyzed intramolecular Pauson–Khand reaction for the stereoselective construction of cyclopentanone bearing an all-carbon quaternary stereogenic center at the bridge-head position and the light-initiated photocatalysis for convergent and asymmetric cross-coupling of the unstabilized C(sp3)-radical...

read more

147.Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

Sijia Chen†, Chongguo Jiang†, Nan Zheng, Zhen Yang* and Lili Shi* Catalysts, 2020, 10 (10), 1199 Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five...

read more

146.Synthesis of 4-Desmethyl-Rippertenol and 7-Epi-Rippertenol via Photoinduced Cyclization of Dienones

Zi-Chun Zhang†, Dan-Dan Zhao†, Zhong-Chao Zhang, Xin-Yu Tan, Jian-Xian Gong*, Jun-Kai Fu* & Zhen Yang* Chinese Chemical Society, 2020, 2(5), 2074–2083 The synthesis of cycloheptanoid-based fused polycyclic frameworks is a challenge for organic chemists due to unfavorable entropic factors and ring strains. Herein, a concise synthesis of 4-desmethyl-rippertenol and 7-epi-rippertenol bearing a unique, [6,6,5,7]-fused tetracyclic framework is reported. The route features a novel photoinduced intramolecular cyclization of α-cyclopropyl dienone followed by an unexpected thermal...

read more

Group Family 2019

read more

郑楠%Research Associate

郑楠 Nan Zheng, Ph. D. Education & Experience 2020-now Research Associate, Peking University. 2017-2020 Postdoctoral Research Associate, University of Utah & Stanford University, Mentor: Prof. Danny Chou & Prof. J. Michael McIntosh. 2012-2017 Ph.D.in Chemical Genetics, Peking University, Mentor: Prof. Zhen Yang. 2008-2012 B.S. in Pharmacy, Sichuan University, Advisor: Prof. Jinsong Yang. Awards & Honors 2019 Excellent Poster Award of 14th Annual Peptide Therapeutics Symposium 2019 American Diabetes Association (ADA) Postdoctoral Fellowship 2017 Merit Student of Peking...

read more

刘汝东%625309731@qq.com%Nanjing University

刘汝东 Peking University Education B.S.:School of Chemistry and Chemical Engineering,Nanjing University

read more

唐福%Tong_328@stu.pku.edu.cn%Jinan University

唐福 Education B.S. (2016-2020) : Department of Chemistry, Jinan University (Advisor: Prof. Shihai Xu) PhD. (2020-now) : School of Chemical Biology and Biotechnology, Shenzhen Graduate School, Peking University. Advisor: Prof. Zhen Yang, Prof. Jianxian Gong and Prof. Jun Huang.

read more

王荣亚%wangrongya0401@163.com%Zhengzhou University

王荣亚 Peking University   Education B.S.(2016-2020):Zhengzhou University Pharmacy College,Zhengzhou Henan Ph.D.(2020-new):School of Chemical Biology & Biotechnology,Shenzhen Graduate School, Peking University. Advisor : Prof. Zhen Yang , Prof. Jianxian Gong and Prof. Jun Huang.

read more

145.Asymmetric Total Synthesis of (−)-Spirochensilide A

Xin-Ting Liang, Jia-Hua Chen,* and Zhen Yang* J. Am. Chem. Soc. 2020, 142(18), 8116–8121 An asymmetric total synthesis of (−)-spirochensilide A has been achieved for the first time. The synthesis features a semipinacol rearrangement reaction to stereoselectively construct the two-vicinal quaternary chiral centers at C8 and C10, a tungsten-mediated cyclopropene-based Pauson–Khand reaction to install the C13 quaternary chiral center, and a furan-based oxidative cyclization to stereoselectively form the spiroketal...

read more

144.Photoredox‐Catalyzed Isomerization of Highly‐Substituted Allylic Alcohols via C‐H bond activation

Kai Guo, Zhongchao Zhang, Anding Li, Yuanhe Li, Jun Huang,* Zhen Yang,* Angew. Chem. Int. Ed.2020, 59(28), 11660-11668 •C−H Activation | Hot Paper  Photoredox‐catalyzed isomerization of γ‐carbonyl‐substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time via C‐H bond activation . This catalytic redox‐neutral process provided a way for the synthesis of 1,4‐dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transferred into their corresponding carbonyl compounds. The density functional...

read more

143.Asymmetric Total Synthesis of (+)-Waihoensene

Yongzheng Qu, Zheyuan Wang, Zhongchao Zhang, Wendou Zhang, Jun Huang,* and Zhen Yang* J. Am. Chem. Soc. 2020, 142(14), 6511-6515 • Highlighted in ChemistryViews, 07 Apr 2020 The asymmetric total synthesis of (+)-waihoensene, which has a cis-fused [6,5,5,5] tetracyclic core bearing an angular triquinane, a cis-fused six-membered ring, and four contiguous quaternary carbon atoms, was achieved through a sequence of chemical reactions in a stereochemically well-defined manner. The total synthesis features the following: (1) Cu-catalyzed asymmetric conjugated 1,4-addition; (2)...

read more

142.Asymmetric Total Synthesis of (−)-Guignardones A and B

Zhiming Yan, Chunbo Zhao, Jianxian Gong,* and Zhen Yang* Org. Lett. 2020, 22(4), 1644-1647 The asymmetric total synthesis of (−)-guignardones A (2) and B (1) has been accomplished. The highly oxidized 6-oxabicyclo[3.2.1]octane core was constructed from d-quinic acid via substitution/desulfurization reaction with thiophenol to forge the bridged ring scaffold, and a Pummerer rearrangement and 1,4-addition/elimination sequence was employed to install the β-carbonyl group at the congested C-1 position. A late-stage Knoevenagel condensation–6π-electrocyclization and directed hydrogenation...

read more

141.Protecting-Group-Free Total Syntheses of (±)-Norascyronones A and B

Tingting Cao, Lei Zhu, Yu Lan*, Jun Huang* and Zhen Yang* Org. Lett. 2020, 22(7), 2517-2521 Protecting-group-free total syntheses of natural products norascyronone A and norascyronone B were accomplished in eight steps from the commercially available starting material 1-bromo-4-methoxy-2-methylbenzene. The key step was a Mn/Cu-mediated oxidative cascade annulation reaction that formed the tetracyclic core of the target molecules bearing vicinal bridge-head all-carbon quaternary chiral centers. Our investigation indicated that the C5 stereogenic center of norascyronone C plays a critical role...

read more

于海昕%Postdoctoral Research Associate

于海昕 Haixin YU College of Chemistry and Molecular Engineering Peking University 202 Chengfu Road Beijing 100871, China Tel: 86–17701380102 E-mail: haixinyu@pku.edu.com   Education 2013.9 – 2019.7   Ph.D., Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Study, Peking University, Beijing, China. Research projects: total syntheses of Schisandra nortriterpenoids natural products propindiactone G, 19-dO-arisandilactone A, pre-schisanartanin C. Supervisor: Prof. Zhen Yang, Prof. Jiahua Chen. 2011.8 – 2013.7   M.S., As a joint training...

read more

140.Retro-metal-ene versus retro-Aldol: mechanistic insight into Rh-catalysed formal [3+2] cycloaddition

Song Liu, Tao Zhang, Lei Zhu, Kangbao Zhong, Jianxian Gong, Zhen Yang*, Ruopeng Bai*, Yu Lan* Chem. Commun., 2018,54(96), 13551-13554 Theoretical calculations have been performed to investigate the mechanism and stereoselectivity of rhodium-catalysed intramolecular [3+2] cycloaddition for construction of a substituted hexahydropentalene complex. A new C–C bond cleavage mechanism, retro-Aldol-type, is proposed and verified for this Rh-catalysed [3+2] cycloaddition...

read more

139.Concise gram-scale synthesis of Euphorikanin A skeleton through a domino ring-closing metathesis strategy

Linlin Shi, Yingdong He, Jianxian Gong *, Zhen Yang * Chem. Commun. 2020,56(4), 531-534 Euphorikanin A is a diterpenoid possessing a highly congested and unprecedented 5/6/7/3-fused tetracyclic ring skeleton. To access the challenging chemical structure of Euphorikanins, an efficient total synthetic approach is described. The stereoselective synthesis of the core structure of Euphorikanin A has been achieved from a simple dienyne building block, and a domino ring-closing metathesis (RCM) strategy was used for the gram-scale synthesis of the highly strained Euphorikanin A core. This paves the...

read more

138.Asymmetric Total Synthesis of Pre-schisanartanin C

Yan-Long Jiang, Hai-Xin Yu, Yong Li, Pei Qu, Yi-Xin Han, Jia-Hua Chen*, Zhen Yang* J. Am. Chem. Soc.2020, 142(1), 573-580 Pre-schisanartanin C belongs to the family of Schisandra nortriterpenoids with potent antihepatitis, antitumor, and anti-HIV activities. This paper presents the enantioselective total synthesis of pre-schisanartanin C (1). An important step in the total synthesis of 1 is gold-catalyzed intramolecular cyclopropanation of an 1,8-enyne substrates bearing a secondary ester group at the propargylic position to prepare a bicyclo[6.1.0]nonane core. Additional highlights include...

read more

137.Asymmetric Total Synthesis of (−)-Pavidolide B via a Thiyl-Radical-Mediated [3 + 2] Annulation Reaction

Pengpeng Zhang, Yuanhe Li, Zhiming Yan, Jianxian Gong*, Zhen Yang* J. Org. Chem. 2019, 84(24), 15958-15971 The development of an efficient strategy for the asymmetric total synthesis of the bioactive marine natural product (−)-pavidolide B is described in detail. The development process and detours leading to the key thiyl-radical-mediated [3 + 2] annulation reaction, which constructed the central C ring with four contiguous stereogenic centers in one step, are depicted. Subsequently, the seven-membered D ring is constructed via a ring-closing metathesis reaction followed by a...

read more

136.Diastereoselective Construction of All-Carbon Quaternary Stereocenters via Intramolecular Oxidative Cross-Coupling Reaction

Wei Chen, Renyu Guo, Jianxian Gong*, Zhen Yang* Chin. J. Org. Chem. 2019, 39 (1), 238-248 The formation of sterically hindered C—C bond represents a great challenge in modern synthetic organic chemistry. A particularly challenging issue is the construction of all-carbon quaternary stereocenters. Herein, a ceric ammonium nitrate (CAN)-mediated intramolecular oxidative cross-coupling of silyl ethers for direct construction of valuable polycyclic scaffolds is described. The reaction enables sterically congested vicinal all-carbon quaternary and tertiary stereocenters to be installed...

read more

135.Concise synthesis of the core structure of madreporanone by Rh-catalyzed [3+2] cycloaddition

Rong Long, Zhen Yang* Tetrahedron 2019, 75 (12), 1746-1750 A model study toward total synthesis of madreporanone, a novel diterpene isolated from Azorella madreporica, was investigated. The [3.3.0] bicyclic core of madreporanone bearing a cis-configured isopropyl group and two vicinal quaternary carbon centers was stereoselectively constructed via an intramolecular Rh-catalyzed [3 + 2] cycloaddition in a single...

read more

134.Pd-Catalyzed Decarboxylative Allylation for Stereoselective Syntheses of Allylic Alcohols bearing a Quaternary Carbon Center

Linlin Shi, Yingdong He, Jianxian Gong*, Zhen Yang* Asian J. Org. Chem 2019, 8 (6), 823-827 Olefins play a vital role in the fields of bioscience, medicine, and chemistry. Stereo‐defined olefins are important resource in both chemical laboratory and industry. Using a palladium‐catalyzed decarboxylative transformation of vinyl cyclic carbonates, we have developed an efficient and reliable method for the direct construction of highly substituted olefins with the concomitant formation of a new Csp3‐Csp3 bond. The desired olefins could be generated in reasonable yields with good...

read more

133.Total syntheses of dehydrobotrydienal, dehydrobotrydienol and 10-oxodehydrodihydrobotrydial

Zichun Zhang, Dandan Zhao, Yingdong He, Zhen Yang, Jianxian Gong Chin. Chem. Lett. 2019, 30 (8), 1503-1505 In this paper, we report the concise total syntheses of three botryane sesquiterpenoids: dehydrobotrydienal, dehydrobotrydienol, and 10-oxodehydrodihydrobotrydial. The key transformations include tandem Co-tetramethylthiourea-catalyzed Pauson–Khand and 6π-electrocyclization reactions to forge the tricyclic core structure of the botryanes, and further oxidative aromatization and oxidation to complete the total...

read more

132.Theoretical prediction on the reactivity of the Co-mediated intramolecular Pauson-Khand reaction for constructing bicyclo-skeletons in natural products

LeiZhu, ZheyuanWang, SongLiu, TaoZhang, ZhenYang, RuopengBai, YuLan Chin. Chem. Lett. 2019, 30 (4), 889-894 The Co2(CO)8-mediated intramolecular Pauson-Khand reaction is an efficient approach for constructing polycyclic skeletons. Recently, some of us reported a series of this type reactions involving sterically-hindered enynes for synthesizing natural products with reasonable reaction rates and yields. However, the reason for the high reactivity of the reaction remains unclear. We employed density functional theory calculations to clarify the mechanism and reactivity for this reaction. In...

read more

曹婷婷%13971494906@163.com%Peking University

曹婷婷 13971494906@163.com Peking University   Education Graduate Student (2017-now) : School of Chemical biology & Biotechnology , Shenzhen graduate school , Peking University. Advisors : Prof. Zhen Yang , Prof. Jun Huang.  

read more

王超%1443122184@qq.com%Shaan Xi Normal university

  王超 1901111859@pku.edu.cn   Education: B.S:Northwest university M.S:Shaan Xi Normal university Graduate Student(2019-now):School of Chemical biology&Biotechnology,Shenzhen graduate school, Peiking University Advisor : Prof. Zhen Yang , Prof. Jianxian Gong and Prof. Jun Huang.

read more

杨锦峰%JinFengYang@pku.edu.cn% HuBei University

杨锦峰 JinFengYang@pku.edu.cn     Education: B.S.(2015-2019) HuBei University Graduate Student(2019-now):School of Chemical biology&Biotechnology,Shenzhen graduate school, Peiking University Advisor : Prof. Zhen Yang , Prof. Jianxian Gong and Prof. Jun Huang.

read more