Total synthesis of (-)-norzoanthamine

Angew Chem Int Ed Engl. 2009;48(8):1404-6. doi: 10.1002/anie.200804546.

Abstract

No bones about it: (-)-Norzoanthamine, a promising candidate for an anti-osteoporotic drug, was the target of a total synthesis (see scheme). The final bisaminal formation with AcOH/H(2)O gave the DEFG ring, while the cyclization precursor was prepared by installing the remaining bisaminal unit after oxidative cleavage of the cyclopentanol moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Azepines / chemical synthesis*
  • Azepines / chemistry
  • Cyclopentanes / chemistry
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Ketones / chemistry
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism

Substances

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