Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine

Bruno Dudot; Laurent Micouin; Isabelle Baussanne; Jacques Royer

doi:10.1055/s-1999-3434

Synthesis 1999; 1999(4): 688-694
DOI: 10.1055/s-1999-3434

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Asymmetric Routes Towards Polyfunctionalized Pyrrolidines: A Short Diastereoselective Synthesis of Polyhydroxylated Pyrrolidines and an Indolizidine

Bruno Dudot^* , Laurent Micouin, Isabelle Baussanne, Jacques Royer

^*Institut de Chimie des Substances Naturelles, CNRS, F-91198 Gif-sur-Yvette cedex, France; Fax +33(1)69 07 72 47; E-mail: jacques.royer@icsn.cnrs-gif.fr

Abstract

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Various (2S,3S,4R)-2-[(1R)-1-hydroxyalkyl]pyrrolidine-3,4-diols (11) have been prepared in 8 steps and 13-20% overall yields starting from (R)-(-)-phenylglycinol. This concise approach is based on the condensation of a chiral silyloxypyrrole with aldehydes which gave the (R,R)-aldol compounds in good yields and high diastereoselectivities. The cis-hydroxylation followed by reduction and deprotection gave the desired trihydroxylated pyrrolidines. The same strategy has been successively applied to a formal synthesis of 8a-epi-swainsonine.

aldol condensation - OsO₄ hydroxylation - polyhydroxy pyrrolidines and indolizidine - 8-epi-swainsonine

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