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

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.

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.

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

Referências bibliográficas

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Como citar:

Lagreca, María Eugenia; Seoane, Gustavo; Brovetto, Margarita; "Chemoenzymatic Approach to the stereoselective synthesis of C6-C13 fragment of Amphidinolides T Series", p-78-78. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0078-1