Dean V. Johnson, H. Griengl
Jan 13, 1997
Citations
0
Influential Citations
31
Citations
Journal
Tetrahedron
Abstract
Abstract (S)-13-hydroxyoctadeca-(9Z, 11E)-dienoic acid (1) was synthesized in nine steps starting from (E)-2-octenal (2). The (S)-hydroxynitrile lyase cloned from Hevea brasiliensis, that has been overexpressed in Pichia pastoris, was used to interconvert 2 into (S)-cyanohydrin 3. The subsequent butyrate 6 was rearranged using the palladium-bis-(acetonitrile)-dichloride to give the unsaturated nitrile 7 which was fully elaborated to the hydroxy acid 1 in an overall 11% yield and with 99% e.e.