Effects of temperature and concentration in some ring closing metathesis reactions

Kana Yamamoto, Kaustav Biswas, Christoph Gaul, Samuel J. Danishefsky

Research output: Contribution to journalArticle

64 Citations (Scopus)

Abstract

Ring closing metathesis (RCM) has emerged as a powerful tool to construct macrocyclic ring systems. However, the product distribution of monomer and oligomers is often a problem in the formation of medium to large rings. In the course of synthetic studies on the natural product radicicol and its analogs, we have found that the reaction temperature, along with concentration, has significant impact on the outcome of the product ratio. Specifically, carrying out the RCM reaction in refluxing toluene (110°C) at higher dilution affords improved yields of the monomeric macrocycle. Similar observations for another family of macrolactone natural products, the epothilones, are also reported.

Original languageEnglish
Pages (from-to)3297-3299
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number16
DOIs
Publication statusPublished - 2003 Apr 14
Externally publishedYes

Keywords

  • Epothilone
  • Product distribution
  • RCM
  • Radicicol
  • Ring closing metathesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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