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Review
. 2014 Aug 14;50(63):8628-39.
doi: 10.1039/c4cc02290d. Epub 2014 May 15.

Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses

Xiao Wang  1 , Zhiqiang Ma, Xiaolei Wang, Saptarshi De, Yuyong Ma, Chuo Chen
Affiliations
Review

Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses

Xiao Wang et al. Chem Commun (Camb). .

Abstract

The pyrrole-imidazole alkaloids are a group of structurally unique and biologically interesting marine sponge metabolites. Among them, the cyclic dimers have caught synthetic chemists' attention particularly. Numerous synthetic strategies have been developed and various biosynthetic hypotheses have been proposed for these fascinating natural products. We discuss herein the synthetic approaches and the biosynthetic insights obtained from these studies.

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Figures

Fig. 1
Fig. 1
Structures of the representative pyrrole-imidazole alkaloids.
Fig. 2
Fig. 2
Probing the biosynthetic hypotheses of the dimerization of the pyrrole-imidazole alkaloid by biomimetic synthesis.
Fig. 3
Fig. 3
The SET-mediated dimerization biosynthetic hypothesis.
Fig. 4
Fig. 4
The divergent SET-mediated dimerization biosynthetic hypothesis.
Fig. 5
Fig. 5
The Kinnel–Scheuer biosynthetic hypothesis.
Fig. 6
Fig. 6
The total syntheses of sceptrins (5) reported by the Baran and Birman's groups.
Fig. 7
Fig. 7
The total syntheses of ageliferins (9) reported by the Baran and Harran's groups.
Fig. 8
Fig. 8
The synthetic approaches of massadines (6)/axinellamines (7)/Palau'amine (8a) reported by the Overman, Carreira, and Romo groups.
Fig. 9
Fig. 9
The total syntheses of massadines (6)/axinellamines (7)/Palau'amine (8a) reported by the Baran group.
Fig. 10
Fig. 10
Our divergent biomimetic synthetic strategy and the energy diagram of the reaction pathways.
Fig. 11
Fig. 11
Our synthesis of ageliferin (9a).
See this image and copyright information in PMC

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