Synlett 2001; 2001(12): 1965-1967
DOI: 10.1055/s-2001-18784
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

A Highly Efficient and Versatile Synthesis of d- and l-erythro-Sphinganine

Christian Hertweck* , Pavel Šebek, Aleš Svatoš
  • *Hans-Knöll-Institute for Natural Products Research, Beutenbergstrasse 11a, 07745 Jena, Germany; Fax: + 49(3641)656699; E-mail: hertweck@pmail.hki-jena.de
Further Information

Publication History

Publication Date:
04 December 2001 (online)

An expedient convergent synthesis of naturally occurring C18-erythro-sphinganine (dihydrosphingosine, 1) is presented. Chiral protected 2-amino-1,3,4-butanetriol 6 is readily transformed into oxazolinyl oxirane building block 9, which is alkylated by a copper mediated SN2 type nucleophilic substitution with tetradecylmagnesium chloride. This method promises to be suited for large-scale syntheses and for rapid access to sphinganine analogues modified in the backbone.

    >