Literature DB >> 20848010

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

Zhiqiang Ma1, Jianming Lu, Xiao Wang, Chuo Chen.   

Abstract

We propose herein an alternative biosynthetic pathway for palau'amine in order to resolve the stereochemical issue from the original Kinnel-Scheuer hypothesis. Furthermore, we use this revised hypothesis as a guide toward the laboratory synthesis of n class="Chemical">palau'amine.

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Year:  2010        PMID： 20848010      PMCID： PMC2999656          DOI： 10.1039/c0cc02214d

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


  28 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.  Enantioselective strategy to the spirocyclic core of Palau'amine and related bisguanidine marine alkaloids.

Authors:  A S Dilley; D Romo
Journal:  Org Lett       Date:  2001-05-17       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.  Total synthesis of (+/-)-axinellamines A and B.

Authors:  Daniel P O'Malley; Junichiro Yamaguchi; Ian S Young; Ian B Seiple; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Sceptrin as a potential biosynthetic precursor to complex pyrrole-imidazole alkaloids: the total synthesis of ageliferin.

Authors:  Phil S Baran; Daniel P O'Malley; Alexandros L Zografos
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-10       Impact factor: 15.336

6.  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

7.  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

8.  Extending Pummerer reaction chemistry. Synthesis of (+/-)-dibromophakellstatin by oxidative cyclization of an imidazole derivative.

Authors:  Ken S Feldman; Amanda P Skoumbourdis
Journal:  Org Lett       Date:  2005-03-03       Impact factor: 6.005

9.  Mechanism of the vinylcyclobutane rearrangement of sceptrin to ageliferin and nagelamide E.

Authors:  Brian H Northrop; Daniel P O'Malley; Alexandros L Zografos; Phil S Baran; K N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-19       Impact factor: 15.336

10.  Total syntheses of (+/-)-massadine and massadine chloride.

Authors:  Shun Su; Ian B Seiple; Ian S Young; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-12-10       Impact factor: 15.419
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  20 in total

1.  Lessons and revelations from biomimetic syntheses.

Authors:  Mina Razzak; Jef K De Brabander
Journal:  Nat Chem Biol       Date:  2011-11-15       Impact factor: 15.040

2.  Asymmetric synthesis of ageliferin.

Authors:  Xiao Wang; Zhiqiang Ma; Jianming Lu; Xianghui Tan; Chuo Chen
Journal:  J Am Chem Soc       Date:  2011-09-08       Impact factor: 15.419

3.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica.

Authors:  E Paige Stout; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

4.  Syntheses of Cyclic Guanidine-Containing Natural Products.

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

5.  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

6.  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

7.  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

8.  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

9.  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

10.  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
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