A Synthesis of Podocarpic Acid

Thomas A. Spencer, Richard J. Friary, Walter W. Schmiegel, Joseph F. Simeone, David S. Watt

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


Reductive carbomethoxylation of α,β-unsaturated ketone 4 was investigated as a potential route to intermediates, such as keto ester 2, with the podocarpic acid (3) stereochemistry. However, none of the desired 12 and only a low yield of isomeric 15 was obtained. Intermediate 2 was prepared instead from 12 isolated from methylation of 8. Other products from this methylation and several related bicyclic terpenoid substances, such as triols 29 and 30, are described. Methyl dl-podocarpate (40) was synthesized from 2 via Robinson annelation in 13% over-all yield.

Original languageEnglish
Pages (from-to)719-726
Number of pages8
JournalJournal of Organic Chemistry
Issue number2
StatePublished - 1968

ASJC Scopus subject areas

  • Organic Chemistry


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