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Free keywords:
HIV-PROTEASE INHIBITOR; STEREOSELECTIVE SYNTHESIS; BUILDING-BLOCK; KINASE-C; L-SERINE; SPHINGOSINE; DIHYDROSPHINGOSINE; 3-KETOSPHINGANINE; NELFINAVIR; ANALOGSamino alcohols; coupling; natural products; sphingolipids;
stereoselective synthesis;
Abstract:
An expedient convergent synthesis of naturally occurring C-18-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(N)2 type nucleophilic substitution with tetradecyl-magnesium chloride, This method promises to be suited for large-scale syntheses and for rapid access to sphinganine analogues modified in the backbone.
