An O-to-N intramolecular acyl migration in C₁₉-diterpenoid alkaloids

J Asian Nat Prod Res. 2012;14(6):586-91. doi: 10.1080/10286020.2012.680444. Epub 2012 May 9.

Abstract

The O-acyl group at C-1 of two C₁₉-diterpenoid alkaloids 2 and 5 was transferred to the secondary amine nitrogen to form amides 3 and 6 in the basic condition. This kind of O-to-N intramolecular acyl migration could be caused by the near distance between the nucleophilic nitrogen atom and the carbonyl group of the ester at C-1 in the C₁₉-diterpenoid alkaloids, which is consistent with the conformation of rings A and E in the C₁₉-diterpenoid alkaloids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Amines / chemistry
  • Diterpenes / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular

Substances

  • Alkaloids
  • Amines
  • Diterpenes