Dimeric pyrrole–imidazole alkaloids: synthetic approaches and biosynthetic hypotheses

Wang, Xiao; Ma, Zhiqiang; Wang, Xiaolei; De, Saptarshi; Ma, Yuyong; Chen, Chuo

doi:10.1039/c4cc02290d

Cited by 60 publications

(33 citation statements)

References 155 publications

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“…22,29,32,33 Many of these molecules possess anticancer, antimicrobial, antiviral, or immunosuppressive properties. Structurally, oroidin and its debrominated congeners ( 5 ) serve as the building blocks of this family of alkaloids in a way similar to isoprene in the world of terpenoids.…”

Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

“…33,174-180 We have developed a palladium-catalyzed C–H functionalization reaction to enable an efficient synthesis of dibromophakellstatin in 2007. 175 We have also accomplished the asymmetric synthesis of ageliferins ( 11 ) in 2011, using a tandem radical cyclization approach as the key step to construct its cyclohexenyl core.…”

Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

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Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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Naturally occurring guanidine derivatives frequently display medicinally useful properties. Among them, the higher order pyrrole-imidazole alkaloids, the dragmacidins, the crambescidins/batzelladines, and the saxitoxins/tetradotoxins have stimulated the development of many new synthetic methods over the past decades. We provide here an overview of the syntheses of these cyclic guanidine-containing natural products.

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Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

Section: The Higher Order Pyrrole-imidazole Alkaloidsmentioning

confidence: 99%

Syntheses of cyclic guanidine-containing natural products

Chen

2015

Tetrahedron

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“…1,2 Members of this family have been prized for their biological activities, especially as anti-tumors agents, anti-microbial or anti-biofilm agents. 3 Besides their potential utility as therapeutics leads, the community has been fascinated with the genesis of the more structurally complex members of this family from the simple building blocks e.g.…”

Section: Introductionmentioning

confidence: 99%

Exploring hydroamination-cycloaddition-fragmentation sequences to access polycyclicguanidines and vinyl-2-aminoimidazoles

et al. 2017

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The intramolecular hydroamination of a guanidine on an eneyne unit affords a guanidine-substituted diene capable of reacting with dienophiles. These substrates undergo [4+2]-cycloaddition reactions to generate a series of complex cyclic- and spirocyclic-guanidines. Select substrates can further undergo a ring opening-elimination cascade that ultimately reveals a vinyl-2-aminoimidazole. As such this cascade reaction may find application in the synthesis of oroidin-type natural products and their analogues

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“…1). 3,4 Previously, the Baran and the Birman groups each developed a [2+2] photocycloaddition approach to accomplish the total synthesis of 1 . 5,6 The Baran group further demonstrated that 1 could be converted into 3 in a stereospecific manner.…”

Section: Introductionmentioning

confidence: 99%

Syntheses of sceptrins and nakamuric acid and insights into the biosyntheses of pyrrole–imidazole dimers

Wang

Gao

et al. 2015

Org. Chem. Front.

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Sceptrins and nakamuric acid are structurally unique antibiotics isolated from marine sponges. Recent studies suggest that the biosynthesis of these dimeric pyrrole–imidazole alkaloids involves a single-electron transfer (SET)-promoted [2+2] cycloaddition to form their cyclobutane core skeletons. We describe herein the biomimetic syntheses of racemic sceptrin and nakamuric acid. We also report the asymmetric syntheses of sceptrin, bromosceptrin, and dibromosceptrin in their natural enantiomeric form. We further provide mechanistic insights into the pathway selectivity of the SET-promoted [2+2] and [4+2] cycloadditions that lead to the divergent formation of the sceptrin and ageliferin core skeletons. Both the [2+2] and [4+2] cycloadditions are stepwise reactions, with the [2+2] pathway kinetically and thermodynamically favored over the [4+2] pathway. For the [2+2] cycloaddition, the dimerization of pyrrole–imidazole monomers is rate-limiting, whereas for the [4+2] cycloaddition, the cyclization is the slowest step.

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Dimeric pyrrole–imidazole alkaloids: synthetic approaches and biosynthetic hypotheses

Cited by 60 publications

References 155 publications

Syntheses of cyclic guanidine-containing natural products

Syntheses of cyclic guanidine-containing natural products

Exploring hydroamination-cycloaddition-fragmentation sequences to access polycyclicguanidines and vinyl-2-aminoimidazoles

Syntheses of sceptrins and nakamuric acid and insights into the biosyntheses of pyrrole–imidazole dimers

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