Total Synthesis of (±)-Ferruginol and (±)-Hinokione

David L. Snitman, Richard J. Himmelsbach, David S. Watt

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

Stereospecific syntheses of (±)-ferruginol and (±)-hinokione were achieved in which the tricyclic ring system was assembled in the order C → BC → ABC. The key features of the approach involve: (1) the utilization of a lactone bridge as part of an enone protecting group in ring A; (2) the installation of an isopropyl group by the regioselective addition of lithium dimethylcuprate to a cross-conjugated dienone; (3) the elimination of the lactone bridge with concomitant aromatization of ring C; and (4) the reductive methylation of the enone in ring A to install the C-4 geminal dimethyl group and to guarantee the trans fusion of the AB rings.

Original languageEnglish
Pages (from-to)4758-4762
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number25
DOIs
StatePublished - 1978

ASJC Scopus subject areas

  • Organic Chemistry

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