Publications
117.A rhodium-catalyzed tandem reaction of N-sulfonyl triazoles with indoles: access to indole-substituted indanones
An efficient strategy for the synthesis of structurally diverse indole-substituted indanones via a rhodium(II)-catalyzed tandem reaction of N-sulfonyltriazoles with indoles was developed. The reaction involves rhodium(II)-catalyzed denitrogenation of the N-sulfonyltriazoles to form an oxonium ylide, followed by nucleophilic addition of the indoles and subsequent skeletal rearrangement. This strategy provides straightforward access to indanone frameworks bearing quaternary carbon centers.
116.Synthesis of Substituted Benzoxacycles via a Pd(II)-Catalyzed Intramolecular Arylation Reaction of Allylic Alcohols
Jingjie Li, Ceheng Tan, Xinpeng Mu, Jianxian Gong*, Zhen Yang*
Herein a Pd-catalyzed intramolecular allylation reaction of unprotected allylic alcohols was developed, and the reaction proceeded through a Pd(II)-mediated allylic carbocation species formation, followed by a Friedel-Crafts type annulation to afford functionalized chromanes.
115. Biomimetically inspired asymmetric total synthesis of (+)-19-dehydroxyl arisandilactone A
Yi-Xin Han, Yan-Long Jiang, Yong Li, Hai-Xin Yu, Bing-Qi Tong, Zhe Niu, Shi-Jie Zhou, Song Liu, Yu Lan*, Jia-Hua Chen*, Zhen Yang*
Complex natural products are a proven and rich source of disease-modulating drugs and of efficient tools for the study of chemical biology and drug discovery. The architectures of complex natural products are generally considered to represent significant barriers to efficient chemical synthesis. Here we describe a concise and efficient asymmetric synthesis of 19-dehydroxyl arisandilactone A—which belongs to a family of architecturally unique, highly oxygenated nortriterpenoids isolated from the medicinal plant Schisandra arisanensis. This synthesis takes place by means of a homo-Michael reaction, a tandem retro-Michael/Michael reaction, and Cu-catalysed intramolecular cyclopropanation as key steps. The proposed mechanisms for the homo-Michael and tandem retro-Michael/Michael reactions are supported by density functional theory (DFT) calculation. The developed chemistry may find application for the synthesis of its other family members of Schisandraceae nortriterpenoids.
114.Comparative pharmacokinetic profile of cyclosporine (CsA) with a decapeptide and a linear analogue
David A. Price,*Heather Eng, Kathleen A. Farley,b Gilles H. Goetz, Yong Huang, Zhaodong Jiao, Amit S. Kalgutkar, Natasha M. Kablaoui, Bhagyashree Khunte, Spiros Liras, Chris Limberakis， Alan M. Mathiowetz, Roger B. Ruggeri,Jun-Min Quan and Zhen Yang
Org. Biomol. Chem. 2017, 15, 2501
The synthesis and in vivo pharmacokinetic profile of an analogue of cyclosporine is disclosed. An acyclic congener was also profiled in in vitro assays to compare cell permeability. The compounds possess similar calculated and measured molecular descriptors however have different behaviors in an RRCK assay to assess cell permeability.
113.Formal Total Synthesis of (±)-Lycojaponicumin C
Nan Zheng, Lijie Zhang, Jianxian Gong*, and Zhen Yang*
Org. Lett., 2017, 19, 2921–2924
The formal total synthesis of (±)-lycojaponicumin C has been accomplished. Key transformations include a Rh-catalyzed formal [3 + 2] cycloaddition reaction to construct the bicyclic [3.3.0] scaffold bearing two vicinal quaternary carbon centers, a stereoselective γ-hydroxyl directed Michael addition to introduce the vinyl group at a bulky position, and a late-stage ring-closing metathesis reaction to form the cyclohexanone ring.
