The Diaza[5.5.6.6]fenestrane Skeleton-Synthesis of Leuconoxine Alkaloids

Chemistry. 2016 Mar 7;22(11):3600-10. doi: 10.1002/chem.201502228. Epub 2015 Oct 7.

Abstract

Among the Aspidosperma-derived monoterpene indole alkaloids, the leuconoxine subgroup has drawn significant attention from the synthetic community during the past few years. This Minireview summarizes the hitherto six completed total syntheses of leuconoxines emphasizing the different strategies for assembling the key structural motif, an unprecedented diaza[5.5.6.6]fenestrane skeleton. In addition, the proposed biogenetic relationships within the group of these alkaloids are described.

Keywords: fenestrane; indole alkaloids; leuconolam; leuconoxine; natural products.

Publication types

  • Review

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Aza Compounds / chemistry*
  • Azepines / chemistry*
  • Biological Products / chemistry*
  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkaloids
  • Aza Compounds
  • Azepines
  • Biological Products
  • Indole Alkaloids
  • diaza(5.5.6.6)fenestrane
  • leuconoxine
  • leuconolam