Concise entry to both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one based on novel oxidative etherification: Formal synthesis of (+)-sundiversifolide

Muneo Kawasumi, Naoki Kanoh, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

Both enantiomers of 8-oxabicyclo[3.2.1]oct-3-en-2-one (6) have been synthesized from 4-hydroxycyclohept-2-enone (3) on the basis of a novel oxidative cyclo-etherification using PhI(OH)OTs (Koser's reagent). (-)-(1S,5R)-8-Oxabicyclo[3.2.1]oct-3-en-2-one [(-)-6, 95% ee] was expeditiously transformed to (+)-sundiversifolide (1).

Original languageEnglish
Pages (from-to)3620-3623
Number of pages4
JournalOrganic letters
Volume13
Issue number14
DOIs
Publication statusPublished - 2011 Jul 15

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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