Unified Total Synthesis of Pyrroloazocine Indole Alkaloids Sheds Light on Their Biosynthetic Relationship

Fedor M. Miloserdov, Mariia S. Kirillova, Michael E. Muratore, Antonio M. Echavarren

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The total synthesis of seven members of the lapidilectine and grandilodine family of alkaloids has been accomplished in racemic and enantiopure form without protection/deprotection of functional groups. The two key steps, an 8-endo-dig hydroarylation and a 6-exo-trig photoredox cyclization, were catalyzed using gold. A rationale for the formation of the cyclopropane ring of the lundurines is also provided.

Original languageEnglish
Pages (from-to)5393-5400
Number of pages8
JournalJournal of the American Chemical Society
Volume140
Issue number16
Early online date12 Feb 2018
DOIs
Publication statusPublished - 25 Apr 2018

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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