A highly efficient and versatile synthesis of D- and L-erythro-sphinganine

An expedient convergent synthesis of naturally occurring C-18-erythro-sphin ganine (dihydrosphingosine, 1) is presented. Chiral protected 2-amino-1,3,4 -butanetriol 6 is readily transformed into oxazolinyl oxirane building bloc k 9, which is alkylated by a copper mediated S(N)2 type nucleophilic substi tution with tetradecyl-magnesium chloride, This method promises to be suite d for large-scale syntheses and for rapid access to sphinganine analogues m odified in the backbone.