SECONDARY METABOLITES BY CHEMICAL-SCREENING .13. ENANTIOSELECTIVE SYNTHESIS OF DELTA-LACTONES FROM STREPTENOL-A, A CHIRAL BUILDING BLOCK FROM STREPTOMYCES

被引：46

作者：

ROMEYKE, Y ^{[1
]}

KELLER, M ^{[1
]}

KLUGE, H ^{[1
]}

GRABLEY, S ^{[1
]}

HAMMANN, P ^{[1
]}

机构：

[1] HOECHST AG,POSTFACH 800320,W-6230 FRANKFURT,GERMANY

来源：

TETRAHEDRON | 1991年 / 47卷 / 20-21期

关键词：

D O I：

10.1016/S0040-4020(01)86398-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of all four stereoisomers of the secondary metabolite 3-hydroxy-5-decanolide (4a) from Cephalosporium recifei and both enantiomers of massoialactone (5a) by starting from one chiral building block, streptenol A (1a), a secondary metabolite from Streptomyces sp., is described. The key steps of the reaction sequence involve diastereoselective reduction of 1a to syn- or anti-triol 2a and 2b and the regioselective oxidation of the primary hydroxyl group. This reaction furnishes in one step the sigma-lactones 3a and 3b and requires no protecting group.

引用

页码：3335 / 3346

页数：12

共 34 条

[1] STUDIES ON THE SYNTHESIS OF MASSOI-LACTONE AND ITS HOMOLOGUES .2. SYNTHESIS OF NONYN-1-OL-4-CARBOXYLIC ACID-1-LACTONE (MASSOI-LACTONE) [J].