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Synthesis 2020; 52(17): 2572-2578
DOI: 10.1055/s-0040-1707397
paper

Synthesis of (2S,3R,5R)-2-Azido-3,5-dihydroxynonadecane Sphingolipid Analogue

René Momha  ∗
a   Université de Rennes, Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 allée de Beaulieu, 35708 Rennes, France   Email: renemomha@gmail.com
b   AGIR, EA 4294, UFR of Pharmacy, Jules Verne University of Picardie, 80037 Amiens, France
,
Dieudonné Emmanuel Pegnyemb
c   Département de Chimie Organique, Faculté des Sciences, Université de Yaoundé I, BP 812 Yaoundé, Cameroun
,
Paul Mosset
d   Université de Rennes, CNRS, ISCR, UMR 6226, Avenue du Général Leclerc, 35000 Rennes, France
› Author AffiliationsWe are grateful for the financial support from the Agence Universitaire de la Francophonie (AUF), Région Bretagne, Centre national de la recherche scientifique (CNRS) (UMR 6226), and the Université de Rennes 1.
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Abstract

A concise and highly efficient synthesis of an enigmol analogue has been achieved. The synthetic strategy features Jacobsen’s hydrolytic kinetic resolution (HKR) and epoxide opening by alkynyl boranes as the key steps.

Key words

sphingolipid - HKR - epoxide - enigmol - β-hydroxyacetylenes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707397.
  • Supporting Information


Publication History

Received: 10 March 2020

Accepted: 04 May 2020

Publication Date:
18 May 2020 (online)

© Georg Thieme Verlag
Stuttgart · New York

 

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