-
Chem. Eur. J. 2024. 30(17), e202304371
Yuan-He Li,* Jia-Hua Chen, and Zhen Yang*
The Diels–Alder reaction stands as one of the most pivotal transformations in organic chemistry. Its efficiency, marked by the formation of two carbon-carbon bonds and up to four new stereocenters in a single step, underscores its versatility and indispensability in synthesizing natural products and pharmaceuticals. The most significant stereoselectivity feature is the “endo rule”. While thi...
-
Org. Lett. 2024, 26(26), 5403−5408
Xinyu Tan, Zhilin Song, Xinting Liang, Zhenbao Wang, Hongyi Yuan, Zhongchao Zhang,*and Zhen Yang*
A photoredox-based oxidative heterocoupling of enolsilanes to the corresponding 1,4- and 1,6-dicarbonyl compounds was developed by using Mes-Acr+BF4– as the photocatalyst, and oxygen was used as the oxidant. This newly developed chemistry adheres to the principles of atom economy, step economy, and redox economy, making it a concise and efficient method.
-
J. Org. Chem. 2023, 88(15), 10539−10554
Zhenyu Zhang, Wei Zhang, Jun−Chen Tang, Jin−Teng Che, Zhongchao Zhang, Jia−Hua Chen,*and Zhen Yang*
(+)-Haperforin G was synthesizedin 20 steps from commerciallyavailable starting materials. A Co-catalyzed intramolecular Pauson-Khandreaction was used for stereoselective construction of cyclopentanonebearing an all-carbon quaternary stereogenic center at the bridge-headposition. Light-initiated photocatalysis was used for convergent andasymmetric cross-coupling of the unstabilized C(sp(3)) rad...
-
Org. Lett. 2024, 26(15), 2960–2964
Jianyu Long, Rudong Liu, Xinpeng Mu, Zhilin Song, Zhongchao Zhang,* and Zhen Yang*
A novel strategy for the synthesis of Aspidosperma alkaloids has been achieved via a photoredox-initiated [2+2]/retro-Mannich reaction of tryptamine-substituted enaminones as a key step. The developed chemistry has been applied to the construction of the core tetracycle of Aspidosperma alkaloids (±)-aspidospermidine and (±)-limaspermidine
-
J. Am. Chem. Soc.2024, 146(7), 4363–4368
Zheyuan Wang, Zhilin Song, Jun Huang,* and Zhen Yang*
The total syntheses of penicibilaenes A and B are described. The key step is thetBuOK/DMSO-mediated tandem 5-exo–digConia-ene type reaction and 6-exo–digConia-ene type reaction to install the tricyclic [6.3.1.01,5] dodecane core of penicibilaenes from dibutynyl cyclohexanone in a single step, together with a sequence of copper-mediated conjugate addition and Crabtree’s hydrogenation to forge...
-
Chem Asian J. 2023, 18, e20230062
Hao-Yuan Liu, Zhen-Yu Zhang, Yi-Ke Zhou, Jia-Hua Chen, Zhen Yang,* and Yuan-He Li*
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 synthesi...
-
Org. Lett. 2023, 25(13), 2264–2269
Shu-Min Lu, Chao Chen, Chang Liu, Rudong Liu, Jia-Hua Chen,* Zhongchao Zhang,* and Zhen Yang*
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 (4and5) as...
-
Angew. Chem. Int. Ed. 2023, 62(33)
Yuan-He Li, Su-Lei Zhang, Yong Lu, Bo Xiao, Tian-Yu Sun, Qian-Qian Xu, Jia-Hua Chen,* Zhen Yang*
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 di...
-
Tetrahedron Letters 2023, 117 (2023), 154361-154363
Zhiming Yan, Chunbo Zhao, Zhen Yang*, Jianxian Gong*
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)...
-
SCIENTIA SINICA Chimica 2023, 53(3), 277-288
Zhongchao Zhang, Zhen Yang *
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 synt...