Total Syntheses of Highly Oxidized ent-Kaurenoids Pharicin A, Pharicinin B, 7-O-Acetylpseurata C, and Pseurata C: A [5+2] Cascade Approach

被引：89

作者：

He, Chi ^{[1
]}

Hu, Jialei ^{[1
]}

Wu, Yubing ^{[1
]}

Ding, Hanfeng ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Zhejiang, Peoples R China

[2] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2017年 / 139卷 / 17期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; KAURANE DITERPENOIDS; (-)-MAOECRYSTAL V; H FUNCTIONALIZATION; RADICAL CYCLIZATION; ORGANIC-SYNTHESIS; SINGLET OXYGEN; MAOECRYSTAL V; ROUTE; PHYLLOCLADENE;

D O I：

10.1021/jacs.7b02746

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The unprecedented oxidative dearomatization-induced [5+2] cycloaddition/pinacol-type 1,2-acyl migration cascade efficiently generates a quaternary carbon center and assembles the highly oxygenated bicyclo[3.2.1]octane framework of ent-kaurene diterpenoids. By incorporation of the subsequent retro-aldol/aldol process and singlet oxygen ene reaction, this concise and convergent approach has enabled the first asymmetric total syntheses of pharicin A, pharicinin B, 7-O-acetylpseurata C, and pseurata C.

引用

页码：6098 / 6101

页数：4