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
收藏
页码：14892 / 14896
页数：5
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