Dragmacidin E synthesis studies. Preparation of a model cycloheptannelated indole fragment

Org Lett. 2005 Nov 24;7(24):5449-52. doi: 10.1021/ol0522081.

Abstract

[reaction: see text] The conversion of N-2,2-dichloropropionyl indole methyl ester into a tetracyclic cycloheptannelated indole model compound for the synthesis of dragmacidin E was accomplished in 10 steps. Key reactions include a Witkop cyclization to fashion a C-C bond at C(4) of the indole nucleus and a subsequent Dieckmann cyclization to deliver the desired cycloheptanoid ring.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Models, Molecular*
  • Molecular Structure

Substances

  • Indole Alkaloids
  • dragmacidin E