Journal
TETRAHEDRON
Volume 56, Issue 5, Pages 781-790Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(99)01024-8
Keywords
hydroxynitrile lyases; sphingosines; selective coupling
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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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