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Synthesis of 1,19-Aza-1,19-desoxy-avermectin B(1a): The First Avermectin Macrolactam
Peter T. Meinke1, Byron Arison, J. Chris Culberson
1Merck Research Laboratories, Department of Basic Medicinal Chemistry, P.O. Box 2000, Rahway, New Jersey 07065-0900.
The Journal of Organic Chemistry
|October 24, 2001
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.