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

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Chemoenzymatic synthesis of the C14-C21 fragment of the Amphidinolides T Series

Itzaina, Miguel ; Seoane, Gustavo ; Brovetto, Margarita ;

Abstract:

Dinoflagellates of the genus Amphidinium posses a particularly prolific biosynthetic machinery. For instance, over thirty macrolides have been isolated from Amphidinium strains, displaying extremely potent cytotoxicity against tumor cell lines. Among them, the Amphidinolide T family comprises 19-membered macrolactones possessing seven or eight stereogenic centers, a highly substituted tetrahydrofuran ring, an a−hydroxy ketone, an exocyclic methylene group and a homoallylic ester linkage. Due to their high biological activity and intriguing polyoxygenated structure, we became interested in their preparation and designed a chemoenzymatic approach to the C14-C21 fragment, using as starting material cyclohexadienediol 1 produced by biotransformation of bromobenzene, as shown in Fig.1.

Abstract:

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Palavras-chave: Amphidinolides T, chemoenzymatic, stereocontrolled synthesis,

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DOI: 10.5151/chempro-14bmos-R0078-2

Referências bibliográficas
  • [1] Kubota, T.; Iinuma, Y.; Kobayashi, J. Biol.Pharma.Bull. 2006,29,1314.
  • [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:

Itzaina, Miguel; Seoane, Gustavo; Brovetto, Margarita; "Chemoenzymatic synthesis of the C14-C21 fragment of the 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-R0078-2

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