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

All articles of this category 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 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