Enantiospecific Entry to a Common Decalin Intermediate for the Syntheses of Highly Oxygenated Terpenoids

Shota Nagasawa, Kerry E. Jones, Richmond Sarpong

Research output: Contribution to journalArticlepeer-review

Abstract

Herein, we describe an enantiospecific route to one enantiomer of a common decalin core that is present in numerous highly oxygenated terpenoids. This intermediate is accessed in eight steps from (R)-carvone, an inexpensive, enantioenriched building block, which can be elaborated to the desired bicycle through sequential Fe(III)-catalyzed reductive olefin coupling and Dieckmann condensation. The same synthetic route may be applied to (S)-carvone to afford the enantiomer of this common intermediate for other applications.

Original languageEnglish
Pages (from-to)12209-12215
Number of pages7
JournalJournal of Organic Chemistry
Volume84
Issue number18
DOIs
Publication statusPublished - 2019 Sep 20

ASJC Scopus subject areas

  • Organic Chemistry

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