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Title: Total synthesis of lamellarin D and analogs library
Author: Álvarez Domingo, Mercedes
Pla Queral, Daniel
Olsen, Christian A.
Marchal, Antonio
Francesch, Andrés
Cuevas, Carmen
Albericio Palomera, Fernando
Keywords: Compostos heterocíclics
Productes naturals marins
Medicaments antineoplàstics
Heterocyclic compounds
Marine natural products
Antineoplastic agents
Issue Date: 2006
Abstract: Larnellarins are a group of marine natural products isolated from the prosobranch mollusc Lamellaria sp., the ascidian Didemnum sp., and the sponge Dendrilla Cactos. Several of them exhibit interesting biological activities. Natural as well as synthetic lamellarins should be excellent candidates for the development of new drugs due to their unique skeletal structure and their important biological activities especially as antitumor agents. Lamelarin O has been recently characterized as a topoisomerase 1-targeted anti tumor agent. A variety of synthetic approaches have been developed for this family of alkaloids. Herein we describe a new route to the synthesis of Lamellarin D, from a methyl 2-pyrrolecarboxylate. Transformation of the starting material into the scaffold, a substituted 5,6-dihydropyrrolo (2,l ­a)isoquinoline (5,6-DHPl), was afforded by N-alkylation followed by intramolecular Heck cyclization. From this scaffold the synthetic strategy is based on two sequential regioselective bromination!Suzuki cross-coupling reactions which permitted the introduction of differently substituted aryl groups on positions 1 and 2 followed by oxidation, deprotection, and lactonization.
Note: Reproducció del document publicat en paper a Electronic Journal of Natural Substances, 2006, vol. 1, Special issue 1, p. 39
It is part of: Electronic Journal of Natural Substances, 2006, vol. 1, Special issue 1, p. 39
ISSN: 1951-6193
Appears in Collections:Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

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