Stereochemical Dichotomy in Two Competing Cascade Processes: Total Syntheses of Both Enantiomers of Spiroxin A

被引：20

作者：

Ando, Yoshio ^{[1
]}

Tanaka, Daisuke ^{[1
]}

Sasaki, Ryota ^{[1
]}

Ohmori, Ken ^{[1
]}

Suzuki, Keisuke ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, 2-12-1 O Okayama, Tokyo 1528551, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 36期

关键词：

cascade reactions; natural product synthesis; photoreactions; redox chemistry; spiroxin A; CARBONYL-COMPOUNDS; GRIGNARD-REAGENTS; CHIRALITY; MEMORY; EXTENSIONS; REACTIVITY; PRINCIPLE; ENTRY;

D O I：

10.1002/anie.201906762

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first total synthesis of the marine antibiotic spiroxin A has been achieved for both enantiomeric forms. The discovery of two competing cascade processes triggered by two orthogonal stimuli, photo-irradiation or acid/base treatment, enabled the divergent conversion of a single chiral, nonracemic bis-quinone into both enantiomers of an advanced intermediate en route to both (-)- and (+)-spiroxin A. The mechanism of the enantiodivergence is discussed.

引用

页码：12507 / 12513

页数：7

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