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A concise and scalable synthesis of high enantiopurity (-)-D-erythro-sphingosine using peptidyl thiol ester-boronic acid cross-coupling.

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. By 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%).

SUBMITTER: Yang H

PROVIDER: S-EPMC2663357 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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A concise and scalable synthesis of high enantiopurity (-)-D-erythro-sphingosine using peptidyl thiol ester-boronic acid cross-coupling.

Yang Hao H Liebeskind Lanny S LS

Organic letters 20070704 16

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. By using this concise route (-)-D-erythro-sphingosine can be prepared on lar ...[more]

PMID: 17608484

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