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Total syntheses of isonaamine C and isonaamidine E

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
52
Issue
44
Identifiers
DOI: 10.1016/j.tetlet.2011.08.030
Keywords
  • Leucetta
  • 2-Aminoimidazole
  • 4
  • 5-Diiodoimidazole
  • Azidation
  • Methylparabanic Acid

Abstract

Abstract The total syntheses of two alkaloids isolated from a marine sponge of the Leucetta sp. have been accomplished in 6 and 7 steps starting from a 4,5-diiodoimidazole derivative. Grignard mediated halogen–metal exchange was used to install the benzyl side chain. C2 substitution was accomplished via lithiation followed by quenching with trisyl azide which provided isonaamine C after hydrogenation. Isonaamidine E was then prepared from isonaamine C via introduction of the hydantoin ring by reaction with an activated parabanic acid derivative.

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