Concise photochemical synthesis of the antimalarial indole alkaloid decursivine

Mark Mascal, Kyle V. Modes, Asuman Durmus

Research output: Contribution to journalArticle

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Abstract

A four-step synthesis of the extracyclic, antimalarial indole natural product decursivine is described starting from commercial piperonyl bromide and serotonin (see scheme). A photoinitiated reaction cascade involving indole radical cation formation, rearrangement, radical recombination, rearomatization, elimination, and diastereoselective auto-acid-catalyzed closure of the dihydrofuran ring combine in a single step to conclude this remarkably efficient synthesis.

Original languageEnglish (US)
Pages (from-to)4445-4446
Number of pages2
JournalAngewandte Chemie - International Edition
Volume50
Issue number19
DOIs
StatePublished - May 2 2011

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Keywords

  • antimalarials
  • indoles
  • natural products
  • photochemistry
  • total synthesis

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

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