Stereoselective syntheses of 1,4-dideoxy-1,4-imino-octitols and novel tetrahydroxyindolizidines

A. T. Carmona, Jose M. Fuentes, Ana L. Winters, P. Vogel, I. Robina, E. R. Garcia, R. Demange

Research output: Contribution to journalArticlepeer-review

50 Citations (SciVal)

Abstract

A new route for the preparation of four new indolizidines, (1R,2S,6S,7S,8aS)- and (1R,2S,6R,7R,8aS)-1,2,6,7-tetrahydroxyindolizidine and (1S,2R,7S,8S,8aR)- and (1S,2R,7R,8R,8aR)-1,2,7,8-tetrahydroxyindolizidine is reported. The synthesis is based on Knoevenagel homologation of the readily available enantiomerically pure pyrrolidin-carbaldehydes 13 and 37 followed by asymmetric dihydroxylation of the subsequent alkenyl pyrrolidines and cyclization of the corresponding imino-octitols. The new indolizidines and their precursors (imino-octitols 20, 25, 26) and indolizidinones 28a and 28b have been tested for inhibitory activities toward 26 glycosidases. The enzymatic inhibition of trans-7-hydroxy-d-(−)-swainsonine toward α-mannosidases is similar to that described for trans-7-hydroxy-l-(+)-swainsonine (11b) toward naringinase (α-l-rhamnosidase from Penicillium decumbens).
Original languageEnglish
Pages (from-to)3874-3883
Number of pages10
JournalJournal of Organic Chemistry
DOIs
Publication statusPublished - 24 Apr 2003

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