ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The synthesis of chiral 12-phenyi(2H)dodecanoic acids as metabolic probes for the evaluation of the stereo-chemical course of the biosynthesis of 1-alkerses from fatty acids in plants and insects is described. The diastereoisomeric (2R, 3R)- or (2S, 3S)-12-phenyl(2,3-2H2)dodecanoic acids 11 are obtained in high chemical and optical yield (〉97% e.e.) from the readily available (E)-12-phenyl(2,3-2H2)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 2H2O or H2O buffer. (2R)- and (2S)-12-phenyl(2-2H)dodecanoic acids 9 (〉97% 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(1-2H) undec-1-enes 16 and 16a as reference compounds are also included.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19890720507
