Scalable synthesis of a mycosamine donor. Overcoming difficult reactivity in allose systems

Jeffrey M. Manthorpe, Alex M. Szpilman, Erick M. Carreira

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

Mycosamine is a dideoxyaminosugar found in medicinally relevant macrolides, including amphotericin B and nystatin. Herein we report a reliable, high yielding, scalable synthesis of a mycosamine donor. A major goal of our approach was to minimize purifications via judicious selection of protecting groups; the inherent properties of the allose framework created some deprotection obstacles that were ultimately solved.

Original languageEnglish
Article numberC06505SS
Pages (from-to)3380-3388
Number of pages9
JournalSynthesis
Issue number19
DOIs
StatePublished - 1 Dec 2005
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • Glycosylations
  • Medicinal chemistry
  • Natural products
  • Protecting groups

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