Concise Total Synthesis of Peyssonnoside A

被引：20

作者：

Chesnokov, Gleb A. ^{[1
]}

Gademann, Karl ^{[1
]}

机构：

[1] Univ Zurich, Dept Chem, CH-8057 Zurich, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2021年 / 143卷 / 35期

基金：

瑞士国家科学基金会;

关键词：

ASYMMETRIC CONJUGATE ADDITION; STEREOSELECTIVE-SYNTHESIS; GRIGNARD-REAGENTS; ACTIVATION; CHEMISTRY; GLYCOSYL; EFFICIENT; ALCOHOLS; ENONES;

D O I：

10.1021/jacs.1c07135

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Peyssonnoside A is a marine-derived sulfated diterpenoid glucoside with a unique 5/6/3/6 tetracyclic skeleton with a highly substituted cyclopropane ring deeply embedded into the structure. Herein, we report the first total synthesis of this natural product in a concise, efficient, scalable, and highly diastereoselective fashion. The aglucone peyssonnosol was synthesized in 21% overall yield after 15 steps, featuring a Simmons-Smith cyclopropanation and Mukaiyama hydration, fully controlled by the spatial structure of the substrates.

引用

页码：14083 / 14088

页数：6

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