Enantioselective total synthesis of (+)-ophiobolin A

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

The enantioselective total synthesis of (+)-ophiobolin A is described. This total synthesis features the construction of the spiro CD ring of (+)-ophiobolin A through a stereoselective intramolecular Hosomi-Sakurai cyclization reaction, the joining of the A ring to the CD ring by using a reaction reported by Utimoto, and the construction of the ophiobolin eight-membered carbocyclic ring through ring-closing metathesis (RCM), which was performed for the first time in this study. This successful RCM reaction required the use of a substrate that contained either a benzyloxy or a methoxymethoxy group at the C5 position and either an isopropenyl group or its hydroxylated form at the C6 position.

Original languageEnglish
Pages (from-to)5476-5486
Number of pages11
JournalChemistry - A European Journal
Volume19
Issue number17
DOIs
Publication statusPublished - 2013 Apr 22

Keywords

  • cyclization
  • natural products
  • ophiobolin A
  • spiro compounds
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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