Asymmetric Total Syntheses of 8,9-Seco-ent-kaurane Diterpenoids Enabled by an Electrochemical ODI-[5+2] Cascade

被引：14

作者：

Wang, Bingnan ^{[1
]}

Liu, Zhaobo ^{[1
]}

Tong, Zhenzhong ^{[1
]}

Gao, Beiling ^{[1
]}

Ding, Hanfeng ^{[1
,2
]}

机构：

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

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2021年 / 60卷 / 27期

基金：

中国国家自然科学基金;

关键词：

cascade reactions; electrochemistry; sigmatropic rearrangement; terpenoids; total synthesis; CYTOTOXIC 8,9-SECOKAURENE DITERPENOIDS; ANTIBIOTIC KENDOMYCIN; ANTITUMOR-ACTIVITY; SINGLET OXYGEN; RABDOSIA; ROUTE; (-)-O-METHYLSHIKOCCIN; CYCLOADDITIONS; TERPENOIDS;

D O I：

10.1002/anie.202104410

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An electrochemical ODI-[5+2] cascade reaction was developed which enables the rapid assembly of diversely functionalized bicyclo[3.2.1]octadienones from sensitive ethynylphenols. By combining a directed retro-aldol/aldol process, a [2,3]-sigmatropic rearrangement, and an Al(O-iPr)(3)-promoted reductive 1,3-transposition, the asymmetric total syntheses of five 8,9-seco-ent-kauranoids-(-)-shikoccin, (-)-O-methylshikoccin, (-)-epoxyshikoccin, (+)-O-methylepoxyshikoccin, and (+)-rabdo-hakusin-have been achieved in a concise and efficient manner.

引用

页码：14892 / 14896

页数：5