Lewis Acid Catalyzed Displacement of Trichloroacetimidates in the Synthesis of Functionalized Pyrroloindolines

Arijit A. Adhikari, John D Chisholm

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The pyrroloindoline core is found in many natural products. These structures often differ at the C3a position, which may be substituted with an oxygen, nitrogen, or sp3- or sp2-hybridized carbon. Utilizing a trichloroacetimidate leaving group, a diversity-oriented approach to these structures has been developed. The trichloroacetimidate intermediate allows for the rapid incorporation of anilines, alcohols, thiols, and carbon nucleophiles. This method was applied in the synthesis of arundinine and a formal synthesis of psychotriasine.

Original languageEnglish (US)
Pages (from-to)4100-4103
Number of pages4
JournalOrganic Letters
Volume18
Issue number16
DOIs
StatePublished - Aug 19 2016

ASJC Scopus subject areas

  • Biochemistry
  • Medicine(all)
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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