Syntheses of Cecropia Juvenile Hormones by Selective Side-chain Methylation of (E,E)-Farnesol
作者： Arata Yasuda , Shin Tanaka , Hisashi Yamamoto , Hitosi Nozaki
DOI: 10.1246/BCSJ.52.1701
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摘要: The stereoselective route to the title insect hormones (JH-1 & JH-2) depends crucially on epoxidation of allylic alcohols with t-butyl hydroperoxide in presence oxobis(2,4-pentanedionato-O,O′)vanadium(IV). oxidation 2-methyl-1-hepten-3-ol exclusively produces (2R*,3S*) isomerofthe diastereomeric epoxy alcohols. This is converted into (Z)-6-methyl-5-undecene by sequence involving oxirane reaction lithium dibutylcuprate(I) and removal both hydroxyl groups resulting 1,2-diol. Extension series reactions mono- bisoxirane derived from (E,E)-farnesol gives JH-2 JH-1, respectively.
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