Literature DB >> 16562912

Total synthesis of ageladine A, an angiogenesis inhibitor from the marine sponge Agelas nakamurai.

Matthew L Meketa1, Steven M Weinreb.   

Abstract

[reaction: see text] A 12-step total synthesis of the tricyclic heteroaromatic marine metabolite ageladine A has been achieved using a 6pi-azaelectrocyclization and a Suzuki-Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a chloropyridine as key steps.

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Year:  2006        PMID： 16562912     DOI： 10.1021/ol0602304

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


  11 in total

1.  Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.

Authors:  Grant S Buchanan; John B Feltenberger; Richard P Hsung
Journal:  Curr Org Synth       Date:  2010-08-01       Impact factor: 1.975

2.  Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.

Authors:  Sunil K Ghosh; Grant S Buchanan; Quincy A Long; Yonggang Wei; Ziyad F Al-Rashid; Heather M Sklenicka; Richard P Hsung
Journal:  Tetrahedron       Date:  2008-01-28       Impact factor: 2.457

3.  Synthesis and anticancer activities of ageladine A and structural analogs.

Authors:  Yuelong Ma; Sangkil Nam; Richard Jove; Kenichi Yakushijin; David A Horne
Journal:  Bioorg Med Chem Lett       Date:  2009-11-14       Impact factor: 2.823

4.  Pd-catalyzed C-C bond-forming reactions of thymidine mesitylene sulfonate.

Authors:  Soon Bang Kang; Erik De Clercq; Mahesh K Lakshman
Journal:  J Org Chem       Date:  2007-06-27       Impact factor: 4.354

5.  The alkaloid Ageladine A, originally isolated from marine sponges, used for pH-sensitive imaging of transparent marine animals.

Authors:  Ulf Bickmeyer
Journal:  Mar Drugs       Date:  2012-01-19       Impact factor: 6.085

6.  The chemically synthesized ageladine A-derivative LysoGlow84 stains lysosomes in viable mammalian brain cells and specific structures in the marine flatworm Macrostomum lignano.

Authors:  Thorsten Mordhorst; Sushil Awal; Sebastian Jordan; Charlotte Petters; Linda Sartoris; Ralf Dringen; Ulf Bickmeyer
Journal:  Mar Drugs       Date:  2015-02-11       Impact factor: 5.118

7.  A new species of Agelas from the Zanzibar Archipelago, western Indian Ocean (Porifera, Demospongiae).

Authors:  Renata Manconi; Roberto Pronzato; Erica Perino
Journal:  Zookeys       Date:  2016-01-14       Impact factor: 1.546

Review 8.  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

Review 9.  Marine-derived angiogenesis inhibitors for cancer therapy.

Authors:  Ying-Qing Wang; Ze-Hong Miao
Journal:  Mar Drugs       Date:  2013-03-15       Impact factor: 5.118

10.  Reporter dyes demonstrate functional expression of multidrug resistance proteins in the marine flatworm Macrostomum lignano: the sponge-derived dye Ageladine A is not a substrate of these transporters.

Authors:  Kristin Tietje; Georgina Rivera-Ingraham; Charlotte Petters; Doris Abele; Ralf Dringen; Ulf Bickmeyer
Journal:  Mar Drugs       Date:  2013-10-16       Impact factor: 5.118
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