Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans

Stephen Hanessian, Janek Szychowski, J. Pablo Maianti

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

(Chemical Equation Presented) A synthesis of verdamicin C2 and its congener C2a has been accomplished from sisomicin relying on a novel oxidative transformation of an allylic azide to the corresponding α,β- unsaturated aldehyde, and its stereocontrolled elaboration into the intended 5′ side chain of verdamicin C2 and C2a. In vitro antibacterial testing shows that both C6′ epimers in verdamicin C2 and C2a are equally active against a variety of bacterial strains. Oxidation of allylic primary azides, ethers, and esters of 2-substituted dihydro[2H]pyrans with SeO2 leads directly to the corresponding aldehydes.

Original languageEnglish (US)
Pages (from-to)429-432
Number of pages4
JournalOrganic Letters
Volume11
Issue number2
DOIs
StatePublished - Jan 15 2009
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis and comparative antibacterial activity of verdamicin C2 and C2a. A new oxidation of primary allylic azides in dihydro[2H]pyrans'. Together they form a unique fingerprint.

Cite this