Synthesis of sphingadienine-type glucocerebrosides

被引：23

作者：

Murakami, T ^{[1
]}

Shimizu, T ^{[1
]}

Taguchi, K ^{[1
]}

机构：

[1] Natl Inst Mat & Chem Res, Tsukuba, Ibaraki 3058565, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 04期

关键词：

glycolipids; dienes; vinyl-epoxide; coupling reactions;

D O I：

10.1016/S0040-4020(99)01018-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sphinga-4,8-dienine derivatives were synthesized from a vinyl-epoxide 5 via three routes. First, reaction of 5 with 2-dodecenyl cyanocuprate afforded a 1:1 mixture of (4E,8E)- and (4E,8Z)-sphingadienine derivatives in high yield. Second, the (4E,8E)-isomer was selectively synthesized via allylic bromide-allylic sulfone coupling followed by desulfonylation. Third, the (4E,8Z)-isomer was selectively synthesized via S(N)2'-type addition of di(cyanomethyl)copper-lithium followed by Wittig olefination. These synthetic intermediates were converted to sphingadienine-type glucocerebrosides 1a and 1b which have calcium ionophoretic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：533 / 545

页数：13