ENANTIOSELECTIVE FORMATION OF FUNCTIONALIZED 1,3-DISUBSTITUTED ALLENES - SYNTHESIS OF ALPHA-ALLENIC OMEGA-CARBOMETHOXY ALCOHOLS OF HIGH OPTICAL PURITY

被引：76

作者：

GOODING, OW

BEARD, CC

JACKSON, DY

WREN, DL

COOPER, GF

机构：

[1] Institute of Organic Chemistry, Syntex Research, Palo Alto

[2] Department of Chemistry, University of California, Berkeley

来源：

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

关键词：

D O I：

10.1021/jo00003a033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general, high yield synthesis of multigram quantities of the title allenic alcohols is described. Intermediate 5, derived from D-mannitol, was elaborated to both enantiomers (10 and 11) of the antifungal constituent (11) of Sapium japonicum and the lower homologue (16) useful for the synthesis of allenyl prostaglandins. The natural material was thus shown to possess the R configuration. The product allenes were formed in > 94% ee as determined by C-13 NMR spectral analysis of the corresponding Mosher esters.

引用

页码：1083 / 1088

页数：6

共 52 条

[1]

AHMED M, 1982, J CHEM RES SYNOP, V8, P199

[2] DIASTEREOSELECTIVE BETA-ELIMINATION - SYNTHESIS OF CHIRAL ALKOXY-ALLENES [J].