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An asymmetric Maitland-Japp reaction: a highly enantioselective synthesis of tetrahydropyran-4-ones

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JournalTetrahedron
DatePublished - 8 Jul 2011
Issue number27-28
Volume67
Number of pages7
Pages (from-to)4960-4966
Original languageEnglish

Abstract

A highly enantioselective synthesis of functionalized tetrahydropyran-4-ones has been achieved by the development of a catalytic asymmetric Maitland-Japp reaction using Chan's diene as the nucleophile. This reaction has been used to synthesize the tetrahydropyran ring of (-)-centrolobine and the C9-C19 tetrahydropyran ring of (+)-phorboxazole B. (C) 2011 Elsevier Ltd. All rights reserved.

    Research areas

  • Tetrahydropyran-4-ones, Asymmetric, Maitland-Japp reaction, Chan's diene, TRANSANNULAR CONJUGATE ADDITION, ONE-POT, CONSTRUCTION, COMPLEX, (+/-)-CENTROLOBINE, CONDENSATION, PRODUCTS, CONCISE, CORE

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