Literature DB >> 16805527

Direct access to marine pyrrole-2-aminoimidazoles, oroidin, and derivatives, via new acyl-1,2-dihydropyridin intermediates.

Cosima Schroif-Gregoire1, Nathalie Travert, Anne Zaparucha, Ali Al-Mourabit.   

Abstract

[reaction: see text] A short synthesis of the C(11)N(5) oroidin derivatives is reported. The key step of the strategy is a one-pot oxidative bromine-mediated addition of protected guanidines to the N-acyl-1,2-dihydropyridines 9a-c. The new N-acyl-1,2-dihydropyridines were prepared directly from pyridine and pyrrole-2-carbonyl chloride by reduction with borohydride reagent in one step.

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Year:  2006        PMID: 16805527     DOI: 10.1021/ol0608451

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  10 in total

1.  Synthetic Studies on Palau'amine. Construction of the Cyclopentane Core via an Asymmetric 1,3-Dipolar Cycloaddition.

Authors:  Kosuke Namba; Makto Inai; Uta Sundermeier; Thomas J Greshock; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2010-12-15       Impact factor: 2.415

2.  Synthetic access to the chlorocyclopentane cores of the proposed original and revised structures of palau'amine.

Authors:  Michael S Bultman; Jun Ma; David Y Gin
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  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

4.  Total synthesis of the natural product (±)-dibromophakellin and analogues.

Authors:  Nicole M Hewlett; Jetze J Tepe
Journal:  Org Lett       Date:  2011-07-28       Impact factor: 6.005

5.  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

6.  Methods for direct alkene diamination, new & old.

Authors:  Sam de Jong; Daniel G Nosal; Duncan J Wardrop
Journal:  Tetrahedron       Date:  2012-03-21       Impact factor: 2.457

7.  Total synthesis of palau'amine.

Authors:  Ian B Seiple; Shun Su; Ian S Young; Chad A Lewis; Junichiro Yamaguchi; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-01       Impact factor: 15.336

8.  Action of clathrodin and analogues on voltage-gated sodium channels.

Authors:  Steve Peigneur; Aleš Zula; Nace Zidar; Fiona Chan-Porter; Robert Kirby; David Madge; Janez Ilaš; Danijel Kikelj; Jan Tytgat
Journal:  Mar Drugs       Date:  2014-04-04       Impact factor: 5.118

Review 9.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118

10.  Total Synthesis of (±)-Sceptrin.

Authors:  Long V Nguyen; Timothy F Jamison
Journal:  Org Lett       Date:  2020-05-07       Impact factor: 6.005

  10 in total

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