STEREOSELECTIVE SYNTHESIS OF THE C(19)-TO-C(27) SEGMENT OF RIFAMYCIN-S

被引：20

作者：

BORN, M ^{[1
]}

TAMM, C ^{[1
]}

机构：

[1] UNIV BASEL,INST ORGAN CHEM,ST JOHANNS RING 19,CH-4056 BASEL,SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1990年 / 73卷 / 08期

关键词：

D O I：

10.1002/hlca.19900730821

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of diester 3, a synthon for the C(19)‐to‐C(27) segment of rifamycin S (1), is described, starting from the meso‐diester 4 (Schemes 2 and 3). Inversion of the configuration at the later C(23) and two aldol condensations with the lithium enolate 18 of 2,6‐dimethylphenyl propionate each producing two new chiral centres of threo‐configuration, led to the desired diester 3. The absolute configuration of the new chiral centres was proven by a single X‐ray analysis of intermediate 19 (Fig.) and by converting diester 3 into meso‐diester 25. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim

引用

页码：2242 / 2250

页数：9

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