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A short radiosynthesis of natural juvenile hormone III, methyl [12-3H]-(10R)-10,11-epoxyfarnesoate

✍ Scribed by Wai-Si Eng; Glenn D. Prestwich

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
304 KB
Volume
25
Category
Article
ISSN
0022-2135

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✦ Synopsis

A new asymmetric synthesis of natural JH III from methyl farnesoate allows introduction of tritium from sodium borotritide into the 12-methyl group. Selective allylic oxidation followed by Shaxpless epoxidation of the (E)-allylic alcohol gives an epoxy alcohol (>97% e.e.), which is oxidized to the aldehyde. Sodium borotritide (65 CUmmol) reduction of the aldehyde is followed by tosylation. iodide displacement, and cyanoborohydride displacement to give [3H]-(lOR)-JH 111, specific activity 14 Ci/mmol.

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