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Preparation of (10R,s-[10-3H]juvenile hormone III and (10R,S,11S,R)-[10-3H]juvenile hormone 0; conversion of [10-3H] juvenile hormone III to methyl (2E,6E)[10-3H]Farnesoate and (2E 6E)- [10-3H] farnesol

✍ Scribed by Fred. C. Baker; David A. Schooley

Publisher
John Wiley and Sons
Year
1986
Tongue
French
Weight
417 KB
Volume
23
Category
Article
ISSN
0022-2135

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✦ Synopsis

Samples of racemic [10-3H] juvenile hormone 111 (methyl (2~,6~)-lO,ll-epoxy-3,7,11-trimethyl-2,6-dodecadienoate) and [lo-3 Hljuvenile hormone 0 (methyl (2E,6~,10~)-3,7-diethyl-l0,1l-epoxy-ll-methyl-2,6-tridecadienoate~were prepared by NaB H4 reduction of the corresponding 1 I-chloro-lo-oxo ("chloroketone") precursors to their respective [10-3H]chlorohydrins, followed by treatment of the latter with potassium carbonate in methanol. [10-3H]Juvenile hormone 111 3 was converted to methyl [lo-3 Hlfarnesoate (methyl (2~,6E)-3,7,11-trimethyl-2,6,10-dodecatrienoate) by reduction with sodium iodide and zinc in acetic acidsodium acetate. aluminum hydride afforded a sample of [lo-Hlfarnesol ((2E,6E)-3,7,1l-trimethyl-2,6,10-dodecatrien-l-ol). Further reduction of methyl [10-3H]farnesoate with diisobutyl 3 Key Words: [10-3H]Juvenile Hormone 111, [10-3H]Juvenile Hormone 0, Methyl [lo-3H]Farnesoate, [ 10-3H]Farnesol, Insect Juvenile Hormones, HPLC. 0362-4803/86/05053>1 IW5.50 @ 1986 by John Wiley & Sons, Ltd.

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