Syntheses of cecropia juvenile hormones by selective side-chain methylation of (E,E)-farnesol.
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The stereoselective route to the title insect hormones (JH-1 & JH-2) depends crucially on the epoxidation of allylic alcohols with <I>t</I>-butyl hydroperoxide in the presence of oxobis(2,4-pentanedionato-<I>O</I>,<I>O</I>′)vanadium(IV). The oxidation of 2-methyl-1-hepten-3-ol exclusively produces the (2<I>R</I><SUP>*</SUP>,3<I>S</I><SUP>*</SUP>) isomerofthe diastereomeric epoxy alcohols. This is converted into (<I>Z</I>)-6-methyl-5-undecene by the sequence involving oxirane reaction with lithium dibutylcuprate(I) and the removal of both hydroxyl groups of the resulting 1,2-diol. Extension of the series of reactions to the mono- and bisoxirane derived from (<I>E</I>,<I>E</I>)-farnesol gives JH-2 and JH-1, respectively.
- Bulletin of the Chemical Society of Japan
Bulletin of the Chemical Society of Japan 52(6), 1701-1704, 1979
The Chemical Society of Japan