SELECTIVE REACTIONS USING N-(TERT-BUTOXYCARBONYL)-2-(TERT-BUTYLDIMETHYLSILOXY)PYRROLE - CONCISE ASYMMETRIC SYNTHESES OF (+)-1-DEOXY-8-EPI-CASTANOSPERMINE AND ITS ENANTIOMER

被引：40

作者：

CASIRAGHI, G

ULGHERI, F

SPANU, P

RASSU, G

PINNA, L

FAVA, GG

FERRARI, MB

PELOSI, G

机构：

[1] CNR,IST APPLICAZ TECN CHIM AVANZATE,I-07100 SASSARI,ITALY

[2] UNIV PARMA,IST CHIM GEN,I-43100 PARMA,ITALY

[3] CNR,CTR STUDIO STRUTTURISTICA DIFFRATTOMETR,I-43100 PARMA,ITALY

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 23期

关键词：

D O I：

10.1039/p19930002991

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Advantage being taken of the versatility of the siloxydiene TBSOP in asymmetric synthesis, (6S,7R,8S,8aR)-6,7,8-trihydroxyindolizidine 11 has been assembled from the L-threose derivative 1 in six or eight steps in 22-30% overall yield. Pivotal to the success of this total synthesis venture is the ready availability of unsaturated lactam 2 with complete stereocontrol. As a corollary, the synthesis of the known indolizidine enantiomer ent-11 confirms the feasibility of the procedure. The structure of compound 5 has been determined by X-ray crystallography.

引用

页码：2991 / 2997

页数：7

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