A biomimetic route for construction of the [4+2] and [3+2] core skeletons of dimeric pyrrole-imidazole alkaloids and asymmetric synthesis of ageliferins

Xiao Wang, Xiaolei Wang, Xianghui Tan, Jianming Lu, Kevin W. Cormier, Zhiqiang Ma, Chuo Chen

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

The pyrrole-imidazole alkaloids have fascinated chemists for decades because of their unique structures. The high nitrogen and halogen contents and the densely functionalized skeletons make their laboratory synthesis challenging. We describe herein an oxidative method for accessing the core skeletons of two classes of pyrrole-imidazole dimers. This synthetic strategy was inspired by the putative biosynthesis pathways and its development was facilitated by computational studies. Using this method, we have successfully prepared ageliferin, bromoageliferin, and dibromoageliferin in their natural enantiomeric form.

Original languageEnglish (US)
Pages (from-to)18834-18842
Number of pages9
JournalJournal of the American Chemical Society
Volume134
Issue number45
DOIs
StatePublished - Nov 14 2012

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ASJC Scopus subject areas

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

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