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

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JournalOrganic and Biomolecular Chemistry
DateE-pub ahead of print - 12 Mar 2015
DatePublished (current) - 28 Apr 2015
Issue number16
Volume13
Number of pages8
Pages (from-to)4743-4750
Early online date12/03/15
Original languageEnglish

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.

    Research areas

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

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