Stereospecific route to 5,11-methanomorphanthridine alkaloids via intramolecular 1,3-dipolar cycloaddition of nonstabilized azomethine ylide: formal total synthesis of (+/-)-pancracine

Org Lett. 2005 Aug 18;7(17):3713-6. doi: 10.1021/ol051321o.

Abstract

The core structure of the complex pentacyclic 5,11-methanomorphanthridine alkaloids is constructed stereospecifically in one step employing an intramolecular [3 + 2]-cycloaddition of nonstabilized azomethine ylide as the key step. The strategy is demonstrated by accomplishing the formal total synthesis of (+/-)-pancracine. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Catalysis
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkaloids
  • Heterocyclic Compounds, 4 or More Rings
  • pancracine