Total Synthesis of (+)-Euphorikanin A via an Atropospecific Cascade

被引：3

作者：

Classen, Moritz J. ^{[1
]}

Kicin, Bilal ^{[1
]}

Ruf, Vincent A. P. ^{[1
]}

Hamminger, Alexander ^{[1
]}

Ribadeau-Dumas, Loelie ^{[1
]}

Amberg, Willi M. ^{[1
]}

Carreira, Erick M. ^{[1
]}

机构：

[1] Swiss Fed Inst Technol, Dept Chem & Appl Biosci, Lab Organ Chem, CH-8093 Zurich, Switzerland

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2023年 / 145卷 / 50期

关键词：

BIOLOGICAL-ACTIVITY; RING; DITERPENES; EUPHORIKANIN; MOIETY;

D O I：

10.1021/jacs.3c11000

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A total synthesis of the ingenane-derived diterpenoid (+)-euphorikanin A is described. Key to the strategy is a stereocontrolled one-pot sequence consisting of transannular aldol addition reaction, hemiketal formation, and subsequent semipinacol rearrangement that efficiently leads to the complete euphorikanin skeleton. Atroposelective ring-closing olefin metathesis proved critical for the stereospecific cascade, leading to formation of a (Z)-bicyclo-[7.4.1]-tetradecenone core. An additional salient feature of the route is pyrolysis of a bis-methylxanthate to cleanly furnish the natural product.

引用

页码：27225 / 27229

页数：5

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