Synthesis of (+)-Lineariifolianone and Related Cyclopropenone-Containing Sesquiterpenoids

Keith P. Reber, Ian W. Gilbert, Daniel A. Strassfeld, Erik J. Sorensen

Research output: Contribution to journalArticle

Abstract

A synthesis of the proposed structure of lineariifolianone has been achieved in eight steps and 9% overall yield starting from (+)-valencene, leading to a reassignment of the absolute configuration of this unusual cyclopropenone-containing natural product. Key steps in the synthetic route include kinetic protonation of an enolate to epimerize the C7 stereocenter and a stereoconvergent epoxide opening to establish the trans-diaxial diol functionality. The syntheses of the enantiomers of two other closely related natural products are also reported, confirming that all three compounds belong to the eremophilane class of sesquiterpenoids.

Original languageEnglish (US)
Pages (from-to)5524-5534
Number of pages11
JournalJournal of Organic Chemistry
Volume84
Issue number9
DOIs
StatePublished - May 3 2019

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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