Total Synthesis of (±)-Poitediol and (±)-Dactylol

Robert C. Gadwood, Renee M. Lett, Jane E. Wissinger

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Abstract

The unusual cyclooctanoid sesquiterpene, poitediol (7), was synthesized in racemic form in 20 steps from 2-methoxy-4-methyl-2-cyclohexen-l-one (14). The key step in the synthesis was the oxy-Cope rearrangement of 5-ethenyl-6-ethynyl-2-methylbicyclo[3.2.0]heptan-6-ol (22) to afford cis-1,2,3,3a,4,8-hexahydro-3-methyl-5H-cyclopentacycloocten-5-one (10). Racemic dactylol (8) was prepared in one step from poitediol by reduction with sodium in liquid ammonia.

Original languageEnglish (US)
Pages (from-to)6343-6350
Number of pages8
JournalJournal of the American Chemical Society
Volume108
Issue number20
DOIs
StatePublished - Jan 1 1986

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