A new and highly stereoselective synthesis of polyhydroxyindolizidines from 4-octulose derivatives

被引：27

作者：

Izquierdo, I ^{[1
]}

Plaza, MT ^{[1
]}

Robles, R ^{[1
]}

Mota, AJ ^{[1
]}

机构：

[1] Univ Granada, Fac Pharm, Dept Organ Chem, E-18071 Granada, Spain

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 06期

关键词：

D O I：

10.1016/S0957-4166(98)00064-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(1S,2S,6R,7R,8R,8aR)-1,2,6,7,8-Pentahydroxyindolizidine 12 and (1R,6R,7R,8R,8aR)-1,6,7,8-tetrahydroxyindolizidine (1,6-diepicastanospermine, 24) have been stereoselectively synthesized from the important key intermediates 1,4-dideoxy-1,4-imino-D-erythro-L-altro-octitol 7 and 1,2,4-trideoxy-1,4-imino-D-glycero-D-talo-octitol 20 in three steps. Compounds 7 and 20 were readily obtained from 2,3:4,5:6,7-tri-O-isopropylidene-beta-D-glycero-D-galacto-oct-4-ulo-4,8-pyranose 1 and 2-deoxy-4,5:6,7-di-O-isopropylidene-beta-D-manno-oct-4-ulo-4,8-pyranose 13 in four steps, respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1015 / 1027

页数：13

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