Synthesis of a C(4)-C(9) eleutheside template from D-glucal

被引：13

作者：

By, K ^{[1
]}

Kelly, PA ^{[1
]}

Kurth, MJ ^{[1
]}

Olmstead, MM ^{[1
]}

Nantz, MH ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 07期

关键词：

eleutheside; epoxide; stereoselective; D-glucal; hexenulose;

D O I：

10.1016/S0040-4020(00)01117-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)-C(9) templates for eleutheside syntheses. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1183 / 1187

页数：5

共 39 条

[1] Addition of organolithium reagents to some carbohydrate enones [J].