Concise entry to chiral 5-(4-Hydroxybutyl)-2(5 H)-furanone via HTIB-mediated novel oxidative fragmentation: Formal total synthesis of (+)-dubiusamine A

Muneo Kawasumi, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The concise synthesis of 5-(4-hydroxybutyl)-2(5H)furanone has been accomplished from 9-oxabicyclo[4.2.1]non-7-en-1-ol on the basis of HTIB [PhI(OH)OTs, a.k.a. Koser's reagent]-mediated novel oxidative fragmentation. Chiral (-)-(R)-5-(4-hydroxy-butyl)-2(5H)-furanone (>99% ee) was used for the formal total synthesis of (+)-dubiusamine A (1).

Original languageEnglish
Pages (from-to)1788-1790
Number of pages3
JournalOrganic letters
Volume15
Issue number7
DOIs
Publication statusPublished - 2013 Apr 5

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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