Synthesis of the isocoumarin portion of the rubromycins

被引：45

作者：

Waters, SP ^{[1
]}

Kozlowski, MC ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 21期

关键词：

isocoumarin; rubromycin; purpuromycin; antitumor; antibiotic;

D O I：

10.1016/S0040-4039(01)00524-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of the isocoumarin found in the rubromycin class of natural products is reported. The isocoumarin ring system is formed via Heck coupling of a pyruvate synthon with a terephthalic acid derivative followed by an intramolecular acid-catalyzed cyclization. The requisite terephthalic acid precursor is generated by carboxylation of catechol and then desymmetrization of the aromatic ring by halogenation. The isocoumarin derivative that has been produced is an appropriate precursor For the synthesis of gamma -rubromycin, purpuromycin. and heliquinomycin. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3567 / 3570

页数：4