A Submarine Journey: the Pyrrole-imidazole Alkaloids

Overview

Journal Mar Drugs

Publisher MDPI

Specialties Biology
Pharmacology

Date 2010 Jan 26

PMID 20098608

Citations 50

Authors

Barbara Forte

Beatrice Malgesini

Claudia Piutti

Francesca Quartieri

Alessandra Scolaro

Gianluca Papeo

Affiliations

Soon will be listed here.

Abstract

In his most celebrated tale "The Picture of Dorian Gray", Oscar Wilde stated that "those who go beneath the surface do so at their peril". This sentence could be a prophetical warning for the practitioner who voluntarily challenges himself with trying to synthesize marine sponge-deriving pyrrole-imidazole alkaloids. This now nearly triple-digit membered community has been growing exponentially in the last 20 years, both in terms of new representatives and topological complexity--from simple, achiral oroidin to the breathtaking 12-ring stylissadines A and B, each possessing 16 stereocenters. While the biosynthesis and the role in the sponge economy of most of these alkaloids still lies in the realm of speculations, significant biological activities for some of them have clearly emerged. This review will account for the progress in achieving the total synthesis of the more biologically enticing members of this class of natural products.

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References

Kock M, Grube A, Seiple I, Baran P . The pursuit of palau'amine. Angew Chem Int Ed Engl. 2007; 46(35):6586-94. DOI: 10.1002/anie.200701798. View

Domostoj M, Irving E, Scheinmann F, Hale K . New total synthesis of the marine antitumor alkaloid (-)-agelastatin A. Org Lett. 2004; 6(15):2615-8. DOI: 10.1021/ol0490476. View

Koenig S, Miller S, Leonard K, Lowe R, Chen B, Austin D . A transient N-O-linked Pauson-Khand strategy for the synthesis of the deschloro carbocyclic core of the palau'amines and styloguanidines. Org Lett. 2003; 5(13):2203-6. DOI: 10.1021/ol0344063. View

Yoshimitsu T, Ino T, Futamura N, Kamon T, Tanaka T . Total synthesis of the beta-catenin inhibitor, (-)-agelastatin A: a second-generation approach based on radical aminobromination. Org Lett. 2009; 11(15):3402-5. DOI: 10.1021/ol9012684. View

Grube A, Kock M . Structural assignment of tetrabromostyloguanidine: does the relative configuration of the palau'amines need revision?. Angew Chem Int Ed Engl. 2007; 46(13):2320-4. DOI: 10.1002/anie.200604076. View

Lovely C, Du H, He Y, Dias H . Oxidative rearrangement of imidazoles with dimethyldioxirane. Org Lett. 2004; 6(5):735-8. DOI: 10.1021/ol036403w. View

Baran P, Zografos A, OMalley D . Short total synthesis of (+/-)-sceptrin. J Am Chem Soc. 2004; 126(12):3726-7. DOI: 10.1021/ja049648s. View

Zollinger M, Mayer P, Lindel T . Total synthesis of the cytostatic marine natural product dibromophakellstatin via three-component imidazolidinone anellation. J Org Chem. 2006; 71(25):9431-9. DOI: 10.1021/jo061813u. View

Wan Y, Hur W, Cho C, Liu Y, Adrian F, Lozach O . Synthesis and target identification of hymenialdisine analogs. Chem Biol. 2004; 11(2):247-59. DOI: 10.1016/j.chembiol.2004.01.015. View

10.

Shengule S, Karuso P . Concise total synthesis of the marine natural product ageladine A. Org Lett. 2006; 8(18):4083-4. DOI: 10.1021/ol061584y. View

11.

Richards J, Reyes S, Stowe S, Tucker A, Ballard T, Mathies L . Amide isosteres of oroidin: assessment of antibiofilm activity and C. elegans toxicity. J Med Chem. 2009; 52(15):4582-5. PMC: 2739084. DOI: 10.1021/jm900378s. View

12.

Longley D, Johnston P . Molecular mechanisms of drug resistance. J Pathol. 2005; 205(2):275-92. DOI: 10.1002/path.1706. View

13.

Zancanella M, Romo D . Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate. Org Lett. 2008; 10(17):3685-8. PMC: 5548495. DOI: 10.1021/ol801289b. View

14.

Belanger G, Hong F, Overman L, Rogers B, Tellew J, Trenkle W . Stereocontrolled synthesis of triazacyclopenta[cd]pentalenes by intramolecular 1,3-dipolar cycloaddition reactions of azomethine imines. J Org Chem. 2002; 67(22):7880-3. DOI: 10.1021/jo026282y. View

15.

Mee S, Lee V, Baldwin J . Significant enhancement of the Stille reaction with a new combination of reagents-copper(I) iodide with cesium fluoride. Chemistry. 2005; 11(11):3294-308. DOI: 10.1002/chem.200401162. View

16.

Trost B, Crawley M . Asymmetric transition-metal-catalyzed allylic alkylations: applications in total synthesis. Chem Rev. 2003; 103(8):2921-44. DOI: 10.1021/cr020027w. View

17.

Richards J, Huigens Iii R, Ballard T, Basso A, Cavanagh J, Melander C . Inhibition and dispersion of proteobacterial biofilms. Chem Commun (Camb). 2008; (14):1698-700. DOI: 10.1039/b719802g. View

18.

Birman V, Jiang X . Synthesis of sceptrin alkaloids. Org Lett. 2004; 6(14):2369-71. DOI: 10.1021/ol049283g. View

19.

Jacquot D, Mayer P, Lindel T . Chiroptical analysis of marine sponge alkaloids sharing the pyrrolopyrazinone core. Chemistry. 2004; 10(5):1141-8. DOI: 10.1002/chem.200305392. View

20.

Tan X, Chen C . Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers. Angew Chem Int Ed Engl. 2006; 45(26):4345-8. DOI: 10.1002/anie.200601208. View