A new approach to neuraminic acid analogues via 1,2-oxazines

Org Lett. 2009 Feb 5;11(3):527-30. doi: 10.1021/ol802514m.

Abstract

A new stereoselective and potentially very flexible (C(5) + C(3) + C(1)) approach to neuraminic acid derivatives and analogues has been established using enantiopure nitrones and alkoxyallenes as C(3) and C(1) building blocks. Substituent OR(2) in position 4 of neuraminic acid analogues is defined by the alkoxyallene employed for the synthesis of the intermediate 1,2-oxazine. Side chain R(1) can be varied by using different precursor nitrones and introduction of different protection groups R(3) at the amino function is also possible.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Neuraminic Acids / chemical synthesis*
  • Neuraminic Acids / chemistry*
  • Oxazines / chemical synthesis*
  • Oxazines / chemistry
  • Stereoisomerism

Substances

  • Neuraminic Acids
  • Oxazines