Synthesis of (−)-okundoperoxide and determination of the absolute configuration of natural (+)-okundoperoxide

Naoki Mori, Daichi Sakoda, Hidenori Watanabe

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The first enantioselective synthesis of (3S,4aR,8aR)-1 (the enantiomer of natural okundoperoxide) has been accomplished. The synthesis features: 1) stereoselective installation of the peroxy functionality (16 → 17); 2) ring opening of peroxyacetal and subsequent intramolecular reaction between the hydroperoxide and the vinyl epoxide to form the peroxy six-membered ring (5 → 1). The absolute configuration of okundoperoxide was determined to be 3R,4aS,8aS by comparing specific rotations of the synthetic sample and the natural product.

Original languageEnglish
Pages (from-to)3884-3886
Number of pages3
JournalTetrahedron Letters
Volume58
Issue number40
DOIs
Publication statusPublished - 2017 Jan 1
Externally publishedYes

Keywords

  • Antibacterial
  • Antimalarial
  • Determination of the absolute configuration
  • Endoperoxide
  • Okundoperoxide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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