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

Christian Hertweck; Pavel Šebek; Aleš Svatoš

doi:10.1055/s-2001-18784

Synlett 2001; 2001(12): 1965-1967
DOI: 10.1055/s-2001-18784

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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

Abstract

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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 S_N2 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.

amino alcohols - coupling - natural products - sphingolipids - stereoselective synthesis

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