Microwave-enhanced synthesis of N-shifted buflavine analogues via a Suzuki-ring-closing metathesis protocol

Org Lett. 2005 Jun 23;7(13):2723-6. doi: 10.1021/ol050806+.

Abstract

[reaction: see text] A novel, microwave-enhanced six-step synthesis was devised for the synthesis of N-shifted buflavine analogues. Microwave-enhanced Suzuki-Miyaura cross-coupling and ring-closing metathesis reactions were used as the key steps. Microwave irradiation was found to enhance the ring-closing metathesis reaction to generate the otherwise difficultly obtainable medium-sized ring system of the target molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amaryllidaceae Alkaloids / chemical synthesis*
  • Amaryllidaceae Alkaloids / chemistry*
  • Azocines / chemical synthesis*
  • Azocines / chemistry*
  • Combinatorial Chemistry Techniques*
  • Cyclization
  • Microwaves
  • Molecular Structure
  • Plants, Medicinal / chemistry

Substances

  • Amaryllidaceae Alkaloids
  • Azocines
  • buflavine