Journal
ORGANIC LETTERS
Volume 9, Issue 16, Pages 2993-2995Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol070991m
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Funding
- NIGMS NIH HHS [R01 GM066153-22, R01 GM066153, R01 GM066153-20, GM066153, R01 GM066153-21] Funding Source: Medline
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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-OTBS L-serine with E-1-pentadecenyl boronic acid and the highly diastereoselective reduction of the resulting peptidyl ketone with LiAl(O-t-Bu) H-3. 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%).
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