DIRECT TOTAL SYNTHESES OF FRENOLICIN-B AND KALAFUNGIN VIA HIGHLY REGIOSELECTIVE DIELS-ALDER REACTIONS

被引：48

作者：

KRAUS, GA

LI, J

GORDON, MS

JENSEN, JH

机构：

[1] Department of Chemistry, Iowa State University, Ames

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 05期

关键词：

D O I：

10.1021/jo00110a017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Frenolicin B, an anticoccidial agent, has been synthesized in six steps from ketone 3. Racemic kalafungin, an antifungal agent, has been synthesized in five steps. The key step in both syntheses, a regioselective Diels-Alder reaction, proceeds with complete regiocontrol and in excellent yield. One rationale for the remarkable stereocontrol is that the lactone ring induces ring-puckering in the quinone subunit which, in consort with electrostatic repulsion, contributes to the regioselectivity.

引用

页码：1154 / 1159

页数：6