Toward the total synthesis of ansalactam A

Anastasia Hager, Christian A. Kuttruff, Elena Herrero-Gómez, Dirk Trauner

Research output: Contribution to journalArticlepeer-review

Abstract

Ansalactam A is a recently isolated ansa macrolide containing a spiro-γ-lactam functionality that is structurally distinct from other members of the ansa macrolide family. Herein, we describe synthetic studies toward ansalactam A. A route has been developed for the synthesis of a model system featuring a xanthate, which constitutes a direct precursor for the projected radical cyclization step aimed at the formation of the spiro-γ-lactam moiety of ansalactam A. In this context, a new practical method for the removal of an Evans auxiliary attached to sterically encumbered substrates was developed. The utilization of β-lactones as an acylation reagent, an alternative to commonly used amide coupling reactions, is described.

Original languageEnglish (US)
Pages (from-to)59-62
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number1
DOIs
StatePublished - Jan 1 2014

Keywords

  • Ansamycins
  • Evans auxiliary
  • Natural products
  • Total synthesis
  • β-Lactones

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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