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 Sharpless epoxidation of the (E)‐allylic alcohol gives an epoxy alcohol (>97% e.e.), which is oxidized to the aldehyde. Sodium borotritide (65 Ci/mmol) reduction of the aldehyde is followed by tosylation, iodide displacement, and cyanoborohydride displacement to give [3H]‐(10R)‐JH III, specific activity 14 Ci/mmol.
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Eng et al. (1988) studied this question.
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