Platinum catalyzed 7-endo cyclization of internal alkynyl amides and its application to synthesis of the caprazamycin core

Org Biomol Chem. 2012 Aug 14;10(30):6074-86. doi: 10.1039/c2ob25111f. Epub 2012 Apr 16.

Abstract

The scope and limitations of the platinum catalyzed 7-endo cyclization of internal alkynyl amides were investigated. Substitution of the alkyne with an aryl group gave better results, presumably because it stabilized the transition state. Applying the reaction to a secondary amide, the caprazamycin core was successfully synthesized from commercially available material in eight steps.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Amides / chemistry*
  • Azepines / chemical synthesis*
  • Azepines / chemistry*
  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Platinum / chemistry*

Substances

  • Alkynes
  • Amides
  • Azepines
  • Platinum