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A Concise and Scalable Synthesis of High Enantiopurity (−)-d-erythro-Sphingosine Using Peptidyl Thiol Ester−Boronic Acid Cross-Coupling

Hao Yang and Lanny S. Liebeskind
Org Lett. 2007 August 2; 9(16): 2993–2995.

Abstract

A short and efficient synthesis of high enantiopurity (−)-D-erythro-sphingosine has been achieved in 71% yield over 6 steps from N-Boc-L-serine. The key steps are high yield, racemization-free, palladium-catalyzed, copper(I)-mediated coupling of the thiophenyl ester of N-Boc-O-TBS L-serine with E-1-pentadecenyl boronic acid and the highly diastereoselective reduction of the resulting peptidyl ketone with LiAl(O-t-Bu)3H. Using this concise route (−)-D-erythro-sphingosine can be prepared on large scale and in high enantio and diastereopurity (ee >99%, de up to 99%).

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