Total Synthesis of (±)-Dactylol and Related Studies

Ken S. Feldman, Ming Jung Wu, David P. Rotella

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

The marine sesquiterpene (±)-dactylol was prepared from 2,5-dimethyl-7-(3-methyl-4-pentenyl)tropone in six steps. Salient features of the synthesis include; (1) a stereo-and regioselective intramolecular tropone-alkene [6π + 2π] photocyclization to furnish the dactylol carbocyclic skeleton, (2) a regioselective Baeyer-Villiger oxidation of a bisneopentyl ketone, and (3) a chemoselective 1,4-reduction of a cyclocta-1,3-diene moiety.

Original languageEnglish
Pages (from-to)8490-8496
Number of pages7
JournalJournal of the American Chemical Society
Volume112
Issue number23
DOIs
StatePublished - 1 Jan 1990

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