A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir

Manuel Peifer, Raphaëlle Berger, Valerie W. Shurtleff, Jay C. Conrad, David W.C. Macmillan

Research output: Contribution to journalArticle

44 Scopus citations

Abstract

An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.

Original languageEnglish (US)
Pages (from-to)5900-5903
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number16
DOIs
StatePublished - Apr 23 2014

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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