First enantiospecific total synthesis of the antitubercular marine natural product pseudopteroxazole. Revision of assigned stereochemistry

被引：118

作者：

Davidson, JP ^{[1
]}

Corey, EJ ^{[1
]}

机构：

[1] Harvard Univ, Dept Chem & Chem Biol, Cambridge, MA 02138 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 44期

关键词：

D O I：

10.1021/ja0378916

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise, enantiospecific synthesis of pseudopteroxazole (3), which had originally been assigned structure 1, has been accomplished starting from S-(-)-limonene. The known cyclohexanone 5 was converted in five steps to the alpha,beta-enone 8 by a modified Robinson annulation. Transformation of 8 to the orthogonally protected amino phenol 11 was accomplished by a new modification of the Wolff-Semmler rearrangement. The synthesis was completed by cationic cyclization to form 14 diastereoselectively and subsequent introduction of the terminal oxazole subunit.

引用

页码：13486 / 13489

页数：4

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