Total synthesis of norzoanthamine

Science. 2004 Jul 23;305(5683):495-9. doi: 10.1126/science.1098851. Epub 2004 Jun 17.

Abstract

Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% (an average of 92% yield each step).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids
  • Azepines / chemical synthesis*
  • Azepines / chemistry
  • Azepines / pharmacology
  • Heterocyclic Compounds, 4 or More Rings
  • Molecular Conformation
  • Molecular Structure
  • Oxidation-Reduction
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Quinolines / pharmacology
  • Stereoisomerism

Substances

  • Alkaloids
  • Azepines
  • Heterocyclic Compounds, 4 or More Rings
  • Quinolines
  • norzoanthamine