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Synthesis of all 7αH-guaia-4,11-dien-3-one diastereomers from (+)-dihydrocarvone
Authors:Gonzalo Blay
Affiliation:Departament de Química Orgànica, Facultat de Química, Universitat de València, Dr. Moliner 50, E-46100 Burjassot, València, Spain
Abstract:All four 7αH-guaia-4,11-dien-3-one diastereomers have been synthesized from the common intermediate 1αH,10α-acetoxy-7αH-guaia-4,11-dien-3-one obtained from (+)-dihydrocarvone. The spectral features of the four diasteromers have been correlated and the structure and absolute configuration of 1βH,10βH,7αH-guaia-4,11-dien-3-one isolated from Pleocarphus revolutus has been confirmed.
Keywords:Terpene synthesis   Guaiadienones   (+)-Dihydrocarvone   (&minus  )-1,2-Dehydrocyperone   Deoxygenation   Li-amine reduction
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