lipase-catalyzed regioselective esterification of rapamycin: synthesis of temsirolimus (CCI-779)

Org Lett. 2005 Sep 1;7(18):3945-8. doi: 10.1021/ol0514395.

Abstract

A lipase-catalyzed acylation of the immunosuppressant rapamycin with complete regioselectivity is described. The method was successfully applied to the synthesis of 42-hemiesters and temsirolimus (CCI-779), an investigational oncology drug.[reaction: see text]

MeSH terms

  • Antibiotics, Antineoplastic / chemical synthesis*
  • Catalysis
  • Esterification
  • Lipase / metabolism*
  • Molecular Structure
  • Sirolimus / analogs & derivatives*
  • Sirolimus / chemical synthesis
  • Sirolimus / chemistry*
  • Stereoisomerism

Substances

  • Antibiotics, Antineoplastic
  • temsirolimus
  • Lipase
  • Sirolimus