Application of a 6π-1-azatriene electrocyclization strategy to the total synthesis of the marine sponge metabolite ageladine A and biological evaluation of synthetic analogues

Matthew L. Meketa, Steven M. Weinreb, Yoichi Nakao, Nobuhiro Fusetani

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

(Chemical Equation Presented) A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloroimidazopyridine. In addition, an assessment of the biological activity of a variety of synthetic analogues of ageladine A prepared during this synthesis is described.

Original languageEnglish
Pages (from-to)4892-4899
Number of pages8
JournalJournal of Organic Chemistry
Volume72
Issue number13
DOIs
Publication statusPublished - 2007 Jun 22

ASJC Scopus subject areas

  • Organic Chemistry

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