Synlett 2019; 30(02): 185-188
DOI: 10.1055/s-0037-1610344
letter
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Stereodivergent Synthesis of Jaspine B and 4-epi-Jaspine B from Axially Chiral Allenols

Heba Alnazer
a   SPCMIB, UMR5068 CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, Toulouse, 31062, France   Email: ballereau@chimie.ups-tlse.fr
b   Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli, Lebanon
,
Tessa Castellan
a   SPCMIB, UMR5068 CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, Toulouse, 31062, France   Email: ballereau@chimie.ups-tlse.fr
,
Yahya Salma
b   Laboratory of Applied Chemistry (LAC), Faculty of Science III, Lebanese University, P.O. Box 826, Tripoli, Lebanon
,
Yves Génisson
a   SPCMIB, UMR5068 CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, Toulouse, 31062, France   Email: ballereau@chimie.ups-tlse.fr
,
a   SPCMIB, UMR5068 CNRS-Université Paul Sabatier-Toulouse III, 118 route de Narbonne, Toulouse, 31062, France   Email: ballereau@chimie.ups-tlse.fr
› Author Affiliations

This work was supported by grants (AH) from research projects at the Lebanese University.
Further Information

Publication History

Received: 16 October 2018

Accepted after revision: 07 November 2018

Publication Date:
06 December 2018 (online)


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Abstract

A short enantioselective synthetic route to the cytotoxic marine natural product jaspine B has been developed. A chiral non-racemic primary α-allenol, obtained from pentadecanal, gave access to an enantioenriched 2-tetradecyl-2,5-dihydrofuran as key intermediate. A stereodivergent functionalization of this dihydrofuran allowed access in a few steps to jaspine B and its 4-epimer.

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