Synthesis of 1,19-Aza-1,19-desoxy-avermectin B(1a): The First Avermectin Macrolactam. Academic Article uri icon

Overview

abstract

  • The first synthesis of 1,19-aza-1,19-desoxy-avermectin B(1a) (2) is described. This new macrolactam, prepared efficiently from avermectin B(1a) (1a) in seven steps, was designed to form an intramolecular hydrogen bond between the amide carbonyl and the adjacent C7 tertiary hydroxyl via a six-center hydrogen bonding network. The presence of this intramolecular hydrogen bond is anticipated to confer additional conformational rigidity to the 16-membered macrocycle.

publication date

  • April 17, 1998

Identity

Digital Object Identifier (DOI)

  • 10.1021/jo972094+

PubMed ID

  • 11672123

Additional Document Info

volume

  • 63

issue

  • 8