Literature DB >> 19863148

Benzosceptrins A and B with a unique benzocyclobutane skeleton and nagelamide S and T from Pacific sponges.

Jérôme Appenzeller1, Supriya Tilvi, Marie-Thérèse Martin, Jean-François Gallard, Hoda El-bitar, Elise Tran Huu Dau, Cécile Debitus, Dominique Laurent, Céline Moriou, Ali Al-Mourabit.   

Abstract

Four new dimeric pyrrole-2-aminoimidazole alkaloids have been isolated from the Pacific marine sponges Agelas cf. mauritiana and Phakellia sp. They include the unusual C2 symmetrical benzosceptrins A (4) and B (5), which each possess a unique benzocyclobutane skeleton and nagelamides S (6) and T (7). Their structures and relative configuration were elucidated from spectroscopic data. Plausible biogenetic paths for these compounds are also proposed in this paper.

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Year:  2009        PMID： 19863148     DOI： 10.1021/ol901946h

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


  11 in total

1.  Asymmetric total synthesis of ent-cyclooroidin.

Authors:  Sabuj Mukherjee; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  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

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.  De novo synthesis of benzosceptrin C and nagelamide H from 7-15N-oroidin: implications for pyrrole-aminoimidazole alkaloid biosynthesis.

Authors:  E Paige Stout; Brandon I Morinaka; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2012-03-28       Impact factor: 4.050

5.  Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.

Authors:  Manojkumar R Bhandari; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2011-02-21       Impact factor: 6.005

6.  Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp2)-H Functionalization.

Authors:  Jakub Brześkiewicz; Rafał Loska
Journal:  Org Lett       Date:  2022-05-25       Impact factor: 6.072

7.  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

8.  Synthesis of 7-(15)N-Oroidin and evaluation of utility for biosynthetic studies of pyrrole-imidazole alkaloids by microscale (1)H-(15)N HSQC and FTMS.

Authors:  Yong-Gang Wang; Brandon I Morinaka; Jeremy Chris P Reyes; Jeremy J Wolff; Daniel Romo; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

9.  The marine sponge Agelas citrina as a source of the new pyrrole-imidazole alkaloids citrinamines A-D and N-methylagelongine.

Authors:  Christine Cychon; Ellen Lichte; Matthias Köck
Journal:  Beilstein J Org Chem       Date:  2015-10-29       Impact factor: 2.883

Review 10.  Bioactive Secondary Metabolites from the Marine Sponge Genus Agelas.

Authors:  Huawei Zhang; Menglian Dong; Jianwei Chen; Hong Wang; Karen Tenney; Phillip Crews
Journal:  Mar Drugs       Date:  2017-11-08       Impact factor: 5.118
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