Stereoselective synthesis of the C1-C13 fragment of 2,3-dihydrodorrigocin A

J Org Chem. 2005 Sep 30;70(20):8212-5. doi: 10.1021/jo050942s.

Abstract

[Chemical reaction: see text] The first synthesis of the C1-C13 fragment of 2,3-dihydrodorrigocin A has been achieved from 6-bromohexanoic acid in 14 linear steps and an overall yield of 2%. The configurations of the stereogenic centers C8, C9, and C10 have been determined to be the same as for migrastatin.

MeSH terms

  • Hydroxylation
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Piperidones / chemical synthesis
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Piperidones
  • dorrigocin A