Literature DB >> 21888421

Asymmetric synthesis of ageliferin.

Xiao Wang1, Zhiqiang Ma, Jianming Lu, Xianghui Tan, Chuo Chen.   

Abstract

We describe herein an asymmetric synthesis of ageliferin. A Mn(III)-mediated oxidative radical cyclization reaction was used as the key step to construct the core skeleton of this pyrrole-imidazole dimer. This approach resembles the biogenic [4 + 2] dimerization in an intramolecular fashion.

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Year:  2011        PMID： 21888421      PMCID： PMC3183238          DOI： 10.1021/ja207386q

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  39 in total

1.  Manganese(III)-Based Oxidative Free-Radical Cyclizations.

Authors:  Barry B. Snider
Journal:  Chem Rev       Date:  1996-02-01       Impact factor: 60.622

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.  Spirocycloisomerization of tethered alkylidene glycocyamidines: synthesis of a base template common to the palau'amine family of alkaloids.

Authors:  Hugo Garrido-Hernandez; Masakazu Nakadai; Marc Vimolratana; Qingyi Li; Thomas Doundoulakis; Patrick G Harran
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

4.  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.

Authors:  Manuel A Zancanella; Daniel Romo
Journal:  Org Lett       Date:  2008-08-12       Impact factor: 6.005

5.  Stable 5-substituted cyclopentadienes for the Diels-Alder cycloaddition and their application to the synthesis of palau'amine.

Authors:  Jonathan Hudon; Timothy A Cernak; James A Ashenhurst; James L Gleason
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

6.  Regiocontrol in Mn(III)-mediated oxidative heterobicyclizations: access to the core skeletons of oroidin dimers.

Authors:  Xianghui Tan; Chuo Chen
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-26       Impact factor: 15.336

7.  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 8.  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

9.  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

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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  14 in total

1.  Syntheses of Cyclic Guanidine-Containing Natural Products.

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

2.  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

3.  A simple method for the electrophilic cyanation of secondary amines.

Authors:  Chen Zhu; Ji-Bao Xia; Chuo Chen
Journal:  Org Lett       Date:  2013-12-06       Impact factor: 6.005

4.  An approach for the synthesis of nakamuric acid.

Authors:  Xiaolei Wang; Chuo Chen
Journal:  Tetrahedron       Date:  2015-06-03       Impact factor: 2.457

5.  A biomimetic route for construction of the [4+2] and [3+2] core skeletons of dimeric pyrrole-imidazole alkaloids and asymmetric synthesis of ageliferins.

Authors:  Xiao Wang; Xiaolei Wang; Xianghui Tan; Jianming Lu; Kevin W Cormier; Zhiqiang Ma; Chuo Chen
Journal:  J Am Chem Soc       Date:  2012-11-02       Impact factor: 15.419

6.  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

7.  Total Synthesis of Ageliferin via Acyl N-amidinyliminium Ion Rearrangement.

Authors:  Hui Ding; Andrew G Roberts; Patrick G Harran
Journal:  Chem Sci       Date:  2013-01-01       Impact factor: 9.825

8.  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

9.  Stereocontrolled Formation of a [4.4]Heterospiro Ring System with Unexpected Inversion of Configuration at the Spirocenter.

Authors:  Zhiqiang Ma; Lin You; Chuo Chen
Journal:  J Org Chem       Date:  2016-12-20       Impact factor: 4.354

Review 10.  Dimeric pyrrole-imidazole alkaloids: synthetic approaches and biosynthetic hypotheses.

Authors:  Xiao Wang; Zhiqiang Ma; Xiaolei Wang; Saptarshi De; Yuyong Ma; Chuo Chen
Journal:  Chem Commun (Camb)       Date:  2014-05-15       Impact factor: 6.222
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