Synthesis of the Azetidinyl-Thiazoline Fragment of Vioprolides A and C

被引：8

作者：

Chopin, Nathalie ^{[1
]}

Couty, Francois ^{[1
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ Versailles St Quentin Yvelines, Inst Lavoisier Versailles, Univ Paris, UMR 8180, F-78035 Versailles, France

来源：

LETTERS IN ORGANIC CHEMISTRY | 2010年 / 7卷 / 05期

关键词：

Azetidines; natural products; antifungal metabolites; STRAIGHTFORWARD SYNTHESIS;

D O I：

10.2174/157017810791514814

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of the azetidinyl-thiazoline fragment of the antifungal and cytotoxic macrolides vioprolides A and C is reported. Key steps of the synthesis include formation of the thiazoline by condensation of N-Alloc-trans (2S,4R)-4-methylazetidine-2-carbonitrile with L-cysteine and formation of the four-membered ring by intramolecular alkylation of a suitably protected N-Alloc derivative prepared from (R)-alaninol.

引用

页码：353 / 359

页数：7

共 10 条

[1]

AGAMI C, 1995, B SOC CHIM FR, V132, P808

[2] A straightforward synthesis of enantiopure 2-cyano azetidines from β-amino alcohols [J].