Bioinspired Synthesis of Nortriterpenoid Propindilactone G

被引：40

作者：

Wang, Yu ^{[1
]}

Chen, Bo ^{[1
]}

He, Xubiao ^{[1
]}

Gui, Jinghan ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,CAS Key Lab Synthet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 11期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC TOTAL-SYNTHESIS; SCALABLE SYNTHESIS; MOLECULAR-OXYGEN; ALKYL-ARYL; HYDROPEROXIDES; TRITERPENOIDS; OUABAGENIN; EFFICIENT; OXETANES; ALCOHOLS;

D O I：

10.1021/jacs.0c00363

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise bioinspired synthesis of Schisandra nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suarez remote radical functionalization, a ring expansion enabled by a Wagner-Meerwein rearrangement, a stereoinversion of a tertiary alcohol, and a biomimetic transesterification/oxa-Michael addition cascade. This work also provides experimental evidence of the putative propindilactone G biosynthesis pathway.

引用

页码：5007 / 5012

页数：6

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