Concise synthesis of D-erythro-Sphingosine

ORGN 202

Hao Yang, hyang5@emory.edu and Lanny S. Liebeskind. Department of Chemistry, Emory University, 1515 Dickey DR NE, Atlanta, GA 30322
This concise approach provides a very mild and efficient synthesis of D-erythro-Sphingosine with high total yield (60% in 4 steps or 75% in 6 steps) and high optical purity (>99% e.e. and 99% d.e.). In this new method, commercial available and inexpensive Serine was selected as the starting material. The total process included thio esterification, 1-OH protection, Cross Coupling, deprotection, asymmetric reduction and deprotection.