TOTAL SYNTHESIS OF 1,5-DIDEOXY-1,5-IMINOALDITOLS

被引：43

作者：

RASSU, G

PINNA, L

SPANU, P

CULEDDU, N

CASIRAGHI, G

FAVA, GG

FERRARI, MB

PELOSI, G

机构：

[1] UNIV PARMA,CTR STUDIO STRUTTURA DIFFRATTOMETR,I-43100 PARMA,ITALY

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

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

来源：

TETRAHEDRON | 1992年 / 48卷 / 04期

关键词：

HOMOCHIRAL PIPERIDINES; GLYCOSIDASE INHIBITORS; TOTAL SYNTHESIS; AZAPYRANOSE DERIVATIVES;

D O I：

10.1016/S0040-4020(01)88132-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-hepitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti,cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.

引用

页码：727 / 742

页数：16

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