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 journalArticlepeer-review

28 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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