Chemoenzymatic synthesis of bis-THF rings present in acetogenins

Chemoenzymatic synthesis of bis-THF rings present in acetogenins

Ramos, Juan C.; Brovetto, Margarita; Seoane, Gustavo

Abstract:

Acetogenins belong to a family of natural products of general formula I, endowed with high cytotoxic activity. They contain a cyclic THF core flanked by two long hydrocarbon side chains. In addition to the more common mono-THF, bis-THF structures are also found in nature, and display a similar activity profile. The configuration of the THF rings in natural acetogenins is usually R,R, as found in the bis-THF cores of Asimisin and Guanaconetin, Figure 1. We decided to prepare the bis-THF rings present in these natural products using an iterative strategy based on the iodoetherification of 3-butenyl carbinols, such as 2 and 4, Figure 2.

Acetogenins belong to a family of natural products of general formula I, endowed with high cytotoxic activity. They contain a cyclic THF core flanked by two long hydrocarbon side chains. In addition to the more common mono-THF, bis-THF structures are also found in nature, and display a similar activity profile. The configuration of the THF rings in natural acetogenins is usually R,R, as found in the bis-THF cores of Asimisin and Guanaconetin, Figure 1. We decided to prepare the bis-THF rings present in these natural products using an iterative strategy based on the iodoetherification of 3-butenyl carbinols, such as 2 and 4, Figure 2.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0065-1

Referências bibliográficas

• [1] 1 Alali, F. Q.; Liu, X. X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
• [2] 2 Bermejo, A.; Figadere, B.; Zafra, M.-C.; Barrachina, I., Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269-303

Como citar:

Ramos, Juan C.; Brovetto, Margarita; Seoane, Gustavo; "Chemoenzymatic synthesis of bis-THF rings present in acetogenins", p-65-65. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0065-1