A CONCISE, ENANTIOSELECTIVE SYNTHESIS OF CASTANOSPERMINE

被引：73

作者：

KIM, NS ^{[1
]}

CHOI, JR ^{[1
]}

CHA, JK ^{[1
]}

机构：

[1] UNIV ALABAMA,DEPT CHEM,TUSCALOOSA,AL 35487

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 25期

关键词：

D O I：

10.1021/jo00077a034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereoselective synthesis of the polyhydroxy indolizidine alkaloids castanospermine (1) and 6,7-diepicastanospermine (4) has been achieved starting from the readily available alcohol 8. Subsequent Sharpless asymmetric epoxidation, followed by the azide displacement of the tosyl group gave the epoxy azide 12. The asymmetric dihydroxylation of 12 with (DHQ)2-PHAL gave the triol 13 in good diastereoselectivity. Alcohol protection, followed by reductive double cyclization of the resulting epoxy azide 17 gave 5-indolizidinone 18, which was then uneventfully converted to 1. On the other hand, the use of (DHQD)2-PHAL in the dihydroxylation of 12 provided a stereoselective preparation of 4.

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页码：7096 / 7099

页数：4

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