SYNTHETIC APPROACHES TO MYCELIANAMIDE

被引：14

作者：

BROWN, RFC

MEEHAN, GV

机构：

[1] Department of Chemistry, School of General Studies, Australian National University, Canberra, ACT

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1968年 / 21卷 / 06期

关键词：

D O I：

10.1071/CH9681581

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Attempts to synthesize the benzylidene bis-hydroxamic acid system present in mycelianamide (I; R = OH) by direct carbonyl-methylene condensation were unsuccessful. Nycelianamide dimethyl ether (XXIV) is a very unstable substance, which lost one N-methoxyl group as formaldehyde when heated at 77º for 1 hr. Syntheses of compounds closely related to (XXIV) which depended on the introduction of benzylidene unsaturation by slow thermal elimination of CH3SH or CH3SOH at 80-100° consequently gave instead the laotams (XX-XXII) by secondary elimination of formaldehyde. The structural requirements for this elimination of formaldehyde and the stereochemistry of mycelianamide are discussed. © 1968 CSIRO. All rights reserved.

引用

页码：1581 / &