First Total Synthesis of 12-Hydroxy-13-methylpodocarpa-9, 11, 13-trien-3-one

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A first facile total synthesis of 12-hydroxy-13-methylpodocarpa-9, 11, 13-trien-3-one 9 was accomplished via a strategy of AC→ABC. In the synthetic process, compound 5 was synthesized through Reimer-Teimann reaction, followed by methylation, reduction, dehydration,addition to ethylene epoxide and chlorination. The target compound 9 was finally obtained through the condensation of Grignard reagent of compound 5 with 6, followed by intramolecular cyclization, reduction and demethylation.
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