Literature DB >> 24828265

Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Xiao Wang1, Zhiqiang Ma, Xiaolei Wang, Saptarshi De, Yuyong Ma, Chuo Chen.   

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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Year:  2014        PMID： 24828265      PMCID： PMC4096073          DOI： 10.1039/c4cc02290d

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  112 in total

1.  Enantiospecific formal total synthesis of the tumor and GSK-3 beta inhibiting alkaloid, (-)-agelastatin A.

Authors:  Karl J Hale; Mathias M Domostoj; Derek A Tocher; Ed Irving; Feodor Scheinmann
Journal:  Org Lett       Date:  2003-08-07       Impact factor: 6.005

2.  Extending Pummerer reaction chemistry: application to the assembly of the pentacyclic core of dibromopalau'amine.

Authors:  Ken S Feldman; Ahmed Yimam Nuriye
Journal:  Org Lett       Date:  2010-10-15       Impact factor: 6.005

3.  A short total synthesis of the marine sponge pyrrole-2-aminoimidazole alkaloid (±)-agelastatin A.

Authors:  Petar A Duspara; Robert A Batey
Journal:  Angew Chem Int Ed Engl       Date:  2013-08-22       Impact factor: 15.336

4.  Enantioselective total syntheses of (-)-palau'amine, (-)-axinellamines, and (-)-massadines.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Akifumi Nakamura; Junichiro Yamaguchi; Lars Jørgensen; Rodrigo A Rodriguez; Daniel P O'Malley; Tanja Gaich; Matthias Köck; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

Review 5.  Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids.

Authors:  Ali Al-Mourabit; Manuel A Zancanella; Supriya Tilvi; Daniel Romo
Journal:  Nat Prod Rep       Date:  2011-05-09       Impact factor: 13.423

6.  Revisiting the Kinnel-Scheuer hypothesis for the biosynthesis of palau'amine.

Authors:  Zhiqiang Ma; Jianming Lu; Xiao Wang; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2010-09-16       Impact factor: 6.222

7.  Thermochemical Stability of alpha-Amino-alpha-carbonylmethyl Radicals and Their Resonance As Measured by ESR.

Authors:  Frank M. Welle; Hans-Dieter Beckhaus; Christoph Rüchardt
Journal:  J Org Chem       Date:  1997-02-07       Impact factor: 4.354

8.  Enantioselective total synthesis of (+)-dibromophakellstatin.

Authors:  Karine G Poullennec; Daniel Romo
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

9.  Density functional theory guided design of exo-selective dehydroalanine dienophiles for application toward the synthesis of palau'amine.

Authors:  Timothy A Cernak; James L Gleason
Journal:  J Org Chem       Date:  2007-12-08       Impact factor: 4.354

10.  Oxidative rearrangement of imidazoles with dimethyldioxirane.

Authors:  Carl J Lovely; Hongwang Du; Yong He; H V Rasika Dias
Journal:  Org Lett       Date:  2004-03-04       Impact factor: 6.005
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  18 in total

1.  Rapid access to the core skeleton of the [3 + 2]-type dimeric pyrrole-imidazole alkaloids by triplet ketone-mediated C-H functionalization.

Authors:  Lin You; Chuo Chen
Journal:  Tetrahedron       Date:  2017-12-15       Impact factor: 2.457

2.  Precursor-Guided Mining of Marine Sponge Metabolomes Lends Insight into Biosynthesis of Pyrrole-Imidazole Alkaloids.

Authors:  Ipsita Mohanty; Samuel G Moore; Dongqi Yi; Jason S Biggs; David A Gaul; Neha Garg; Vinayak Agarwal
Journal:  ACS Chem Biol       Date:  2020-07-29       Impact factor: 5.100

3.  Syntheses of Cyclic Guanidine-Containing Natural Products.

Authors:  Yuyong Ma; Saptarshi De; Chuo Chen
Journal:  Tetrahedron       Date:  2015-02-25       Impact factor: 2.457

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

Authors:  Ki-Hyeok Kwon; Anne V Edwards; Miao Yang; Ryan E Looper
Journal:  Tetrahedron       Date:  2017-10-19       Impact factor: 2.457

5.  Isolation, Derivative Synthesis, and Structure-Activity Relationships of Antiparasitic Bromopyrrole Alkaloids from the Marine Sponge Tedania brasiliensis.

Authors:  Lizbeth L L Parra; Ariane F Bertonha; Ivan R M Severo; Anna C C Aguiar; Guilherme E de Souza; Glaucius Oliva; Rafael V C Guido; Nathalia Grazzia; Tábata R Costa; Danilo C Miguel; Fernanda R Gadelha; Antonio G Ferreira; Eduardo Hajdu; Daniel Romo; Roberto G S Berlinck
Journal:  J Nat Prod       Date:  2018-01-03       Impact factor: 4.050

6.  Natural products as inspiration for the development of new synthetic methods.

Authors:  Zhiqiang Ma; Chuo Chen
Journal:  J Chin Chem Soc       Date:  2017-08-09       Impact factor: 1.967

7.  Microbial and Functional Biodiversity Patterns in Sponges that Accumulate Bromopyrrole Alkaloids Suggest Horizontal Gene Transfer of Halogenase Genes.

Authors:  Cintia P J Rua; Louisi S de Oliveira; Adriana Froes; Diogo A Tschoeke; Ana Carolina Soares; Luciana Leomil; Gustavo B Gregoracci; Ricardo Coutinho; Eduardo Hajdu; Cristiane C Thompson; Roberto G S Berlinck; Fabiano L Thompson
Journal:  Microb Ecol       Date:  2018-03-15       Impact factor: 4.552

8.  Syntheses of Sceptrins and Nakamuric Acid and Insights into the Biosyntheses of Pyrrole-Imidazole Dimers.

Authors:  Xiaolei Wang; Yang Gao; Zhiqiang Ma; Rodrigo A Rodriguez; Zhi-Xiang Yu; Chuo Chen
Journal:  Org Chem Front       Date:  2015-08-01       Impact factor: 5.281

Review 9.  An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety.

Authors:  Renzo Rossi; Maurizio Ciofalo
Journal:  Molecules       Date:  2020-11-04       Impact factor: 4.411

10.  Asymmetric Synthesis of Axinellamines A and B.

Authors:  Zhiqiang Ma; Xiao Wang; Yuyong Ma; Chuo Chen
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-08       Impact factor: 15.336
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