Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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Chemoenzymatic Approach to the stereoselective synthesis of C6-C13 fragment of Amphidinolides T Series

Lagreca, María Eugenia ; Seoane, Gustavo ; Brovetto, Margarita ;

Abstract:

In the search for novel bioactive compounds, natural products isolated from marine organisms show a wealth of pharmacological and structural diversity. Amphidinolide-T, marine macrolide, exhibit extremely potent cytotoxicity against tumor cells lines. These natural products are 19- membered macrolides, possessing seven or eight stereogenic centers, a highly substituted tetrahydrofuran ring, an α−hydroxy ketone, an exocyclic methylene group and a homoallylic ester linkage. Due to its high biological activity and intriguing polyoxygenated structure we became interested in its preparation and designed a chemoenzymatic approach to its C6-C13 fragment, using as starting material cyclohexadienediol 1 produced by biotransformation of toluene, as shown in Fig.1.

Abstract:

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Palavras-chave: Amphidinolides T, chemoenzymatic synthesis, stereoselective hydrogenation,

Palavras-chave: ,

DOI: 10.5151/chempro-14bmos-R0078-1

Referências bibliográficas
  • [1] Ireland, C.; Copp, B.; Foster, M.; Mc Donald, A.; Radisky, D.; Swersey, J. In “Marine Biotechnology” Plenum Press: New York, 1993; Vol. 1, cap. I.
  • [2] a)Chakraborty, T. K.; Das, S. Curr. Med. Chem. – Anti-Cancer Agents. 2001, 1, 131. b) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
  • [3] 3 Kobayashi , J.; Kubota, T.; Endo , T.; Tsuda , M. J. Org. Chem. 2001, 66, 134.
  • [4] Carrera I.; Brovetto M.; Seoane G.;Tetrahedron 2007, 63, 4095.
Como citar:

Lagreca, María Eugenia; Seoane, Gustavo; Brovetto, Margarita; "Chemoenzymatic Approach to the stereoselective synthesis of C6-C13 fragment of Amphidinolides T Series", p. 78 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0078-1

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