Divergent and stereocontrolled synthesis of the enamide side chains of oximidines I/II/III, salicylihalamides A/B, lobatamides A/D, and CJ-12,950

Org Lett. 2004 Feb 19;6(4):577-80. doi: 10.1021/ol036381d.

Abstract

[reaction: see text] A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)- and (Z)-vinyl iodides with a protected maleimide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkenes / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Copper / chemistry
  • Cyclization
  • Epoxy Compounds / chemical synthesis*
  • Indicators and Reagents
  • Lactones / chemical synthesis*
  • Macrolides / chemical synthesis*
  • Models, Molecular
  • Molecular Structure
  • Salicylates / chemical synthesis*
  • Stereoisomerism

Substances

  • Alkenes
  • Bridged Bicyclo Compounds, Heterocyclic
  • CJ-12950
  • Epoxy Compounds
  • Indicators and Reagents
  • Lactones
  • Macrolides
  • Salicylates
  • lobatamide A
  • lobatamide D
  • oximidine I
  • oximidine II
  • oximidine III
  • salicylihalamide A
  • Copper