Intramolecular silicon-assisted cross-coupling: Total synthesis of (+)-brasilenyne

Scott E. Denmark, Shyh Ming Yang

Research output: Contribution to journalArticlepeer-review


The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl4 to set a propargylic stereocenter and the successful application of the sequential ring closing metathesis/silicon-assisted intramolecular cross-coupling reaction for construction of the oxonin core structure of 1.

Original languageEnglish (US)
Pages (from-to)15196-15197
Number of pages2
JournalJournal of the American Chemical Society
Issue number51
StatePublished - Dec 25 2002

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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