Enantioselective approaches to potential MetAP-2 reversible inhibitors

J Org Chem. 2005 Mar 18;70(6):2409-12. doi: 10.1021/jo047858h.

Abstract

[reaction: see text] Enantioselective deprotonation of 4-substituted cyclohexanones and highly stereoselective conjugate addition of higher order mixed cuprates were the key steps in a concise synthesis of fumagalone-related molecules. The origin of the (low) biological activity of the new compounds as compared to fumagalone is briefly discussed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminopeptidases / antagonists & inhibitors*
  • Cyclohexanes
  • Cyclohexanones / chemical synthesis*
  • Cyclohexanones / chemistry
  • Cyclohexanones / pharmacology
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Epoxy Compounds / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / pharmacology
  • Fatty Acids, Unsaturated / chemistry
  • Metalloendopeptidases / antagonists & inhibitors*
  • Molecular Conformation
  • Sesquiterpenes
  • Stereoisomerism

Substances

  • Cyclohexanes
  • Cyclohexanones
  • Enzyme Inhibitors
  • Epoxy Compounds
  • Fatty Acids, Unsaturated
  • Sesquiterpenes
  • fumagalone
  • fumagillin
  • Aminopeptidases
  • methionine aminopeptidase 2
  • Metalloendopeptidases