Dual macrolactonization/pyran-hemiketal formation via acylketenes: Applications to the synthesis of (-)-callipeltoside A and a lyngbyaloside B model system

Thomas R. Hoye, Michael E. Danielson, Aaron E. May, Hongyu Zhao

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

Two for one: Thermal generation of acylketenes in diol-containing substrates results in the title transformation. This transformation expands the scope of acylketene macrolactonizations and their application to the synthesis of complex macrolides. Triol and tetraol substrates have also been cyclized in highly regioselective fashion. Additionally, the challenging macrolactonization of a tertiary alcohol was achieved. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)9743-9746
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number50
DOIs
StatePublished - Dec 1 2008

Keywords

  • Acylketenes
  • Alcohols
  • Concerted addition
  • Lactones
  • Regioselectivity

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