Expeditious total syntheses of camptothecin and 10-hydroxycamptothecin

Org Lett. 2008 Dec 4;10(23):5393-6. doi: 10.1021/ol802250y.

Abstract

New expeditious total syntheses of (S)-camptothecin (16% overall yield, 95% ee) and (S)-10-hydroxycamptothecin (14% overall yield, 99% ee) have been accomplished, respectively, starting from readily available and inexpensive materials. Development, optimization, and successful application of the cascade reaction consisting of a pyrrolidine-catalyzed Michael addition, an intramolecular aldol condensation, and an oxidative aromatization, the intramolecular oxa Diels-Alder cycloaddition, and the Sharpless asymmetric dihydroxylation make these two new syntheses more efficient and straightforward.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Camptothecin / analogs & derivatives*
  • Camptothecin / chemical synthesis*
  • Catalysis
  • Kinetics

Substances

  • Amines
  • 10-hydroxycamptothecin
  • Camptothecin