Synthesis of L-epi-capreomycidine derivatives via C-H amination

Org Lett. 2011 Aug 5;13(15):4028-31. doi: 10.1021/ol201527k. Epub 2011 Jul 7.

Abstract

The L-epi-capreomycidine (Cpm) derivatives were efficiently and stereoselectively synthesized via nitrene C-H insertion starting from a readily available D-Tyr. Design of a substrate that takes into account hydrogen bonding is a critical feature in order to achieve high selectivity. Our synthetic strategy could be a new access to epi-Cpm and its derivatives, which are found in several biologically active natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amination
  • Arginine / analogs & derivatives*
  • Arginine / chemistry
  • Carbon / chemistry
  • Catalysis
  • Hydrogen / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • capreomycidine
  • Carbon
  • Hydrogen
  • Arginine