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Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

Research output: Contribution to journalJournal article

Published

  • Amanda C. Evans
  • Deborah A. Longbottom
  • Masato Matsuoka
  • John E. Davies
  • Richard Turner
  • Vilius Franckevicius
  • Steven V. Ley
Journal publication date2009
JournalOrganic & biomolecular chemistry
Journal number4
Volume7
Number of pages14
Pages747-760
Original languageEnglish

Abstract

A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.