100. Synthesis of Chiral 12-Phenyl(2H)dodecanoic Acids: Useful Metabolic Probes for the Biosynthesis of 1-Alkenes from Fatty Acids

Article abstract of DOI:10.1002/hlca.19890720507

The synthesis of chiral 12-phenyl(2H)dodecanoic acids as metabolic probes for the evaluation of the stereochemical course of the biosynthesis of 1-alkenes from fatty acids in plants and insects is described.The diastereoisomeric (2R,3R)- or (2S,3S)-12-phenyl(2,3-(2)H2)dodecanoic acids 11 are obtained in high chemical and optical yield (">" 97percent e.e.) from the readily available (E)-12-phenyl(2,3-(2)H2)dodec-2-enoic acid (10) or (E)-12-phenyldodec-2-enoic acid (10a) by microbial reduction with wet packed cells of Clostridium tyrobutyricum in either (2)H2O or H2O buffer. (2R)- and (2S)-12-phenyl(2-(2)H)dodecanoic acids 9 (">" 97percent e.e.) are accessible from the allylic alcohol 6 via Sharpless epoxidation with (+)-L- or (-)-D-diethyl tartrate.Synthetic routes to the (E)- and (Z)-11-phenyl(1-(2)H) undec-1-enes 16 and 16a as reference compounds are also included.