Total Synthesis of (±)-Dactylol and Related Studies

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

Research output: Contribution to journalArticle

42 Citations (Scopus)

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

Fingerprint

Ketones
Olefins
Oxidation
Sesquiterpenes
Alkenes
Skeleton
dactylol
tropone

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Feldman, Ken S. ; Wu, Ming Jung ; Rotella, David P. / Total Synthesis of (±)-Dactylol and Related Studies. In: Journal of the American Chemical Society. 1990 ; Vol. 112, No. 23. pp. 8490-8496.
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Total Synthesis of (±)-Dactylol and Related Studies. / Feldman, Ken S.; Wu, Ming Jung; Rotella, David P.

In: Journal of the American Chemical Society, Vol. 112, No. 23, 01.01.1990, p. 8490-8496.

Research output: Contribution to journalArticle

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