An abiotic strategy for the enantioselective synthesis of erythromycin B

Paul J. Hergenrother, Anne Hodgson, Andrew S. Judd, Wen Cherng Lee, Stephen F. Martin

Research output: Contribution to journalArticlepeer-review

Abstract

Sweet success: The classical approach to macrolide antibiotics involves a macrocyclization followed by the introduction of the carbohydrate residue(s). Now for the first time, a glycosylated seco-acid (see scheme, left) was cyclized to give an intermediate that was converted into a naturally occurring macrolide, as exemplified by the synthesis of erythromycin B (right).

Original languageEnglish (US)
Pages (from-to)3278-3281
Number of pages4
JournalAngewandte Chemie - International Edition
Volume42
Issue number28
DOIs
StatePublished - Jul 28 2003
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Cyclization
  • Glycosylation
  • Macrolactonization
  • Natural products
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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