An efficient enantioselective total synthesis of a trifluoromethyl analog of blastmycinolactol

P. Veeraraghavan Ramachandran, Kamlesh J. Padiya, M. Venkat Ram Reddy, Herbert C. Brown

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

A novel synthetic strategy for the total synthesis of fluorinated analog of blastmycinolactol has been developed using α-pinene based alkoxyallylboration, chelation controlled diastereoselective reduction, and a single step lactonization of the 1,4-diol to the γ-lactone as key steps.

Original languageEnglish (US)
Pages (from-to)579-583
Number of pages5
JournalJournal of Fluorine Chemistry
Volume125
Issue number4
DOIs
StatePublished - Apr 1 2004

Keywords

  • Alkoxyallylboration
  • Anti-alkylation
  • Chelation controlled diastereoselective reduction
  • Dicyclohexylborane
  • Hydroboration
  • Ley's oxidation
  • α-Pinene

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