Asymmetric total synthesis of cephanolide B

被引：33

作者：

Zhang, Hongyuan ^{[1
]}

He, Haibing ^{[2
]}

Gao, Shuanhu ^{[1
,2
]}

机构：

[1] East China Normal Univ, Shanghai Key Lab Green Chem & Chem Proc, Sch Chem & Mol Engn, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China

[2] East China Normal Univ, Shanghai Engn Res Ctr Mol Therapeut & New Drug De, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 03期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1039/d0qo01195a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of cephanolide B, a complex C-18 Cephalotaxus dinorditerpenoid, is presented for the first time. The synthesis relies on the key hexahydrofluorenone core skeleton (A-B-C ring). A remote hydroxyl group directed hydrogenation strategy was developed to selectively reduce the tetra-substituted enone unit. A sequence of modified transformations, including single electron reduction, Barton-McCombie radical deoxygenation, lactonization, and cation mediated Friedel-Crafts cyclization, were efficiently employed to achieve the target.

引用

页码：555 / 559

页数：5

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