Concise Total Synthesis of Peyssonnoside A

被引：14
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
收藏
页码：14083 / 14088
页数：6
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