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14,15,17-Trinorlabdan-8,13-dione 6 was efficiently synthesized via ozonolysis of (+)-manool (4) followed by treatment with aqueous NaOH in the presence of tetra- n-butylammonium bromide as catalyst. This protocol has the advantages of high yield, mild conditions and simple procedure. Utilizing this strategy, the first enantiospecific synthesis of 13,14-dihydroxy-8,11,13-podocarpatrien-7-one (1), a constituent of Taiwania cryptomerioides and Celastrus paniculatus, was achieved starting from (+)-manool (4) after a four-step sequence in 24% overall yield.

natural product communications

Facile Access to Optically Active Ring C Aromatic Diterpene Derivatives from (+)-Manool. First Synthesis of 13,14-Dihydroxy-8,11,13-podocarpatrien-7-one