A Biomimetic Route for Construction of the [4+2] and [3+2] Core Skeletons of Dimeric Pyrrole-imidazole Alkaloids and Asymmetric Synthesis of Ageliferins

Overview

Journal J Am Chem Soc

Publisher American Chemical Society

Specialty Chemistry

Date 2012 Oct 18

PMID 23072663

Citations 18

Authors

Xiao Wang

Xiaolei Wang

Xianghui Tan

Jianming Lu

Kevin W Cormier

Zhiqiang Ma

Chuo Chen

Affiliations

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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.

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