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Enantioselective Synthesis of Deoxymannojirimycin Based on Sharpless Asymmetric Epoxidation of a Highly Functionalized Allylic Alcohol

✍ Scribed by Marie-Céline Lamas; Max Malacria; Serge Thorimbert

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
278 KB
Volume
2011
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

An efficient enantioselective synthesis of deoxymannojirimicin is reported. It is based on the unusual Sharpless asymmetric epoxidation of a silyl‐substituted allylic 1,4‐amino alcohol coupled with a further highly stereoselective intramolecular aldolization. Both enantiomers of deoxymannojirimicin are available. An orthogonally protected polyhydroxylated piperidine was prepared, which could formally lead to other members of this piperidine family.

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