Highly Diastereoselective Synthesis of D-threo- and D-erythro-Sphingosine from Glycidol

Article abstract of DOI:10.1246/cl.1995.393

D-Threo- and D-erythro-sphingosine, (1) and (2), inhibitors of protein kinase C, have been efficiently synthesized from glycidol through (R)-4-methoxycarbonyloxazolidinone (3) by selective mono-alkylation followed by highly diastereoselective reduction of the tin-substituted pentadecenyl ketone 5.