Dean V. Johnson, U. Felfer, H. Griengl
Jan 28, 2000
Citations
0
Influential Citations
31
Citations
Journal
Tetrahedron
Abstract
Abstract 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.