期刊
TETRAHEDRON
卷 56, 期 5, 页码 781-790出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(99)01024-8
关键词
hydroxynitrile lyases; sphingosines; selective coupling
A chemoenzymatic access to D- or L-sphingosines is presented comprising of a total synthesis of the L-threo-isomer and formal. syntheses of the other three isomers. Key to the development of a general synthetic strategy has been the use of enantiocomplementary hydroxynitrile lyases (Hnls) to yield an enantiomeric pair of starting materials. The (S)-Hnl from Hevea brasiliensis has been used to prepare L-threo-sphingosine in 14 steps and an overall 12% yield. Application of the (R)-Hnl from Prunus amygdalus formally allows synthesis of D-threo- and D-erythro-sphingosines. (C) 2000 Elsevier Science Ltd. All rights reserved.
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