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

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.

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.

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

Referências bibliográficas

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Como citar:

Itzaina, Miguel; Seoane, Gustavo; Brovetto, Margarita; "Chemoenzymatic synthesis of the C14-C21 fragment of the Amphidinolides T Series", p-78-78. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0078-2