Total syntheses of leuconoxine, leuconodine B, and melodinine E by oxidative cyclic aminal formation and diastereoselective ring-closing metathesis

Org Lett. 2014 May 2;16(9):2526-9. doi: 10.1021/ol500903e. Epub 2014 Apr 22.

Abstract

Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Secologanin Tryptamine Alkaloids / chemical synthesis*
  • Secologanin Tryptamine Alkaloids / chemistry
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • Secologanin Tryptamine Alkaloids
  • leuconodine B
  • leuconoxine
  • melodinine E