A Maitland-Japp inspired synthesis of dihydropyran-4-ones and their stereoselective conversion to functionalised tetrahydropyran-4-ones

Paul A. Clarke, Philip B. Sellars, Nadiah Mad Nasir

Research output: Contribution to journalArticlepeer-review

Abstract

The Maitland–Japp reaction has been extended to the synthesis of highly functionalised dihydropyran-4-ones. These dihydropyran-4-ones can in turn be converted stereoselectively into tetrahydropyran-4-ones with tertiary and quaternary stereocentres via the one-pot addition of hydride or carbon nucleophiles and trapping with carbon electrophiles. The utility of this method is demonstrated by providing access to the functionalised tetrahydropyran units present in a component of the Civet fragrance and the anticancer polyketide lasonolide A.
Original languageEnglish
Pages (from-to)4743-4750
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number16
Early online date12 Mar 2015
DOIs
Publication statusPublished - 28 Apr 2015

Keywords

  • TETRAHYDROPYRANS
  • MAITLAND-JAPP REACTION
  • LASONOLIDE-A
  • Civet cat secretion

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