CHEMISTRY OF OXAZIRIDINES .16. A SHORT, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE AB-RING SEGMENTS OF GAMMA-RHODOMYCINONE AND ALPHA-CITROMYCINONE USING (+)-[(8,8-DIMETHOXYCAMPHORYL)SULFONYL]OXAZIRIDINE

被引：53

作者：

DAVIS, FA

KUMAR, A

CHEN, BC

机构：

[1] Department of Chemistry, Drexel University, Philadelphia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 03期

关键词：

D O I：

10.1021/jo00003a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient procedure for the preparation of rhodomycinone 1 AB synthons (-)-2a and (+)-2b in high enantiomeric purity (93-4% ee) and good yield is described. This method involves asymmetric oxidation of the lithium enolate of 2-ethyl-5,8-dimethoxy-1-tetralone (4) with (+)-[(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (5c), a new enantiomerically pure, aprotic oxidizing reagent. Lower stereoselectivities were observed with this reagent for the enantioselective oxidation of 2-substituted 1-tetralone enolates 8 lacking the 8-methoxy group.

引用

页码：1143 / 1145

页数：3

共 21 条

[1]

Arcamone F., 1982, DOXORUBICIN ANTICANC

[2]

BROADHURST MJ, 1985, CHEM IND-LONDON, P106

[3] CONVENIENT AB-RING SEGMENTS FOR ANTHRACYCLINONE SYNTHESIS VIA BISHYDROXYLATION OF 2-ETHYL-5,8-DIMETHOXY-7-BROMO-1-TETRALONE [J].