A new access route to functionalized cispentacins from norbornene β-amino acids

Chemistry. 2013 Feb 4;19(6):2102-7. doi: 10.1002/chem.201203183. Epub 2012 Dec 19.

Abstract

An efficient and simple new stereocontrolled access route to novel disubstituted cispentacin derivatives with multiple stereogenic centers from norbornene β-lactam has been developed. The synthesis involves olefinic bond functionalization by dihydroxylation followed by oxidative ring cleavage and transformation of the dialdehyde intermediate through a Wittig reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry*
  • Cycloleucine / analogs & derivatives*
  • Cycloleucine / chemical synthesis
  • Cycloleucine / chemistry
  • Enzymes / chemistry*
  • Norbornanes / chemistry*
  • Oxidation-Reduction
  • Stereoisomerism
  • beta-Lactams / chemistry*

Substances

  • Aldehydes
  • Amino Acids
  • Enzymes
  • Norbornanes
  • beta-Lactams
  • Cycloleucine
  • cispentacin