Abstract
A total synthesis of ageladine A has been achieved by exploiting a Pictet−Spengler-type condensation between 2-aminohistamine and 4,5-dibromo-2-formylpyrrole as the key step.
Citing Articles
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This article has been cited by 5 ACS Journal articles (5 most recent appear below).
A One-Pot Synthesis and Biological Activity of Ageladine A and Analogues
Sudhir R. Shengule, Wendy L. Loa-Kum-Cheung, Christopher R. Parish, Mélina Blairvacq, Laurent Meijer, Yoichi Nakao, and Peter KarusoJournal of Medicinal Chemistry2011 54 (7), 2492-2503A One-Pot Synthesis and Biological Activity of Ageladine A and Analogues
Sudhir R.Shengule, Wendy L.Loa-Kum-Cheung, Christopher R.Parish, MélinaBlairvacq, LaurentMeijer, YoichiNakao, and PeterKarusoJournal of Medicinal Chemistry2011 54 (7), 2492-2503A one-pot synthesis of ageladine A and analogues is reported. The key Pictet−Spengler reaction between 2-aminohistamine and aryl aldehydes has been successfully utilized for the synthesis of the natural product and 14 analogues. These compounds were ...
Synthetic Approaches to the Microtubule-Stabilizing Sponge Alkaloid Ceratamine A and Desbromo Analogues
Matt Nodwell, Alban Pereira, Jenna L. Riffell, Carla Zimmerman, Brian O. Patrick, Michel Roberge and Raymond J. AndersenThe Journal of Organic Chemistry2009 74 (3), 995-1006Synthetic Approaches to the Microtubule-Stabilizing Sponge Alkaloid Ceratamine A and Desbromo Analogues
MattNodwell, AlbanPereira, Jenna L.Riffell, CarlaZimmerman, Brian O.Patrick, MichelRoberge and Raymond J.AndersenThe Journal of Organic Chemistry2009 74 (3), 995-1006Two synthetic approaches to the microtubule-stabilizing ceratamine alkaloids are described. The first approach involved attempts to graft an aminoimidazole moiety onto an azepine ring to form partially hydrogenated versions of the unprecedented aromatic ...
Application of a 6π-1-Azatriene Electrocyclization Strategy to the Total Synthesis of the Marine Sponge Metabolite Ageladine A and Biological Evaluation of Synthetic Analogues
Matthew L. Meketa, Steven M. Weinreb, Yoichi Nakao, and Nobuhiro FusetaniThe Journal of Organic Chemistry2007 72 (13), 4892-4899Application of a 6π-1-Azatriene Electrocyclization Strategy to the Total Synthesis of the Marine Sponge Metabolite Ageladine A and Biological Evaluation of Synthetic Analogues
Matthew L.Meketa, Steven M.Weinreb, YoichiNakao, and NobuhiroFusetaniThe Journal of Organic Chemistry2007 72 (13), 4892-4899A 12-step synthesis of the angiogenesis inhibitory marine metabolite ageladine A is reported. The key steps include a 6π-1-azatriene electrocyclization for formation of the pyridine ring and a Suzuki−Miyaura coupling of N-Boc-pyrrole-2-boronic acid with a ...
Enzyme Inhibitors from Marine Invertebrates
Yoichi Nakao and Nobuhiro FusetaniJournal of Natural Products2007 70 (4), 689-710Enzyme Inhibitors from Marine Invertebrates
YoichiNakao and NobuhiroFusetaniJournal of Natural Products2007 70 (4), 689-710Marine invertebrates are rich sources of small molecules with unique chemical skeletons and potent bioactivities. Historically, such compounds were discovered mainly through the use of assays for phenotype-oriented activities, such as cytotoxicity or ...
A New Total Synthesis of the Zinc Matrixmetalloproteinase Inhibitor Ageladine A Featuring a Biogenetically Patterned 6π-2-Azatriene Electrocyclization
Matthew L. Meketa and Steven M. WeinrebOrganic Letters2007 9 (5), 853-855
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