Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine

The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of thes...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: F. Compostella, F. Ronchetti, L. Franchini, G. B. Giovenzana, L. Panza, D. Prosperi
Other Authors: G.B. Giovenzana
Format: Article in Journal/Newspaper
Language:English
Published: 2002
Subjects:
Settore BIO/10 - Biochimica
Antarc*
Antarctica
Online Access:http://hdl.handle.net/2434/182029
http://www.scopus.com/inward/record.url?eid=2-s2.0-0037094745&partnerID=40&md5=646d94d4c75b018bf79198baf5c88bd9
https://doi.org/10.1016/S0957-4166(02)00201-X
Description
Summary:The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield.

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