Enantioselective total synthesis of (+)-ophiobolin A

Kazuhiro Tsuna, Naoyoshi Noguchi, Masahisa Nakada*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

50 Citations (Scopus)


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
Issue number17
Publication statusPublished - 2013 Apr 22


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

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Organic Chemistry


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