Hydroboration by Diborane of Methyl Abietate
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Hydroboration-oxidation of methyl abietate by diborane in THF occurred preferentially at the sterically unhindered β-side of the molecule without involving the ester. The known hydroboration-oxidation product methyl 7β-hydroxy-13α-isopropylpodocarp-8(14)-en-15α-oate and previously unknown methyl 7β-hydroxy-13-isopropyl-8β-podocarp-13(14)-en-15α-oate, 14β-hydroxy-13α-isopropylpodocarp-7(8)-en-15α-oate, and 7β,14-dihydroxy-13α-isopropyl-8β-podocarpan-15α-oate, i.e., products from monohydroboration-oxidation at the ∆7,8- and ∆13,14-bonds without their respective shifts and from dihydroboration, were obtained.
Keywordsmethyl abietate diborane-THF complex mono- and dihydroboration
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