A tandem ring-closing/cross-coupling metathesis reaction toward the short synthesis of goniothalamin analogs

A tandem ring-closing/cross-coupling metathesis reaction toward the short synthesis of goniothalamin analogs

Bruder, Marjorie; Pilli, Ronaldo Aloise

Abstract:

In view of preparing furanone analogs – exemplified by compound 1- of the cytotoxic naturally occurring styryl lactone goniothalamin (2), we envisioned a key cross-coupling metathesis reaction between vinyl furanone 3 and a range of styrenes. Inspired by the work of Piva et al, where 3 would be formed in situ via ring-closing metathesis of triene 4, we herein report the short synthesis of a variety of styryl furanones using a key tandem ringclosing/ cross-coupling metathesis (RCM/CCM) step.

In view of preparing furanone analogs – exemplified by compound 1- of the cytotoxic naturally occurring styryl lactone goniothalamin (2), we envisioned a key cross-coupling metathesis reaction between vinyl furanone 3 and a range of styrenes. Inspired by the work of Piva et al, where 3 would be formed in situ via ring-closing metathesis of triene 4, we herein report the short synthesis of a variety of styryl furanones using a key tandem ringclosing/ cross-coupling metathesis (RCM/CCM) step.

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DOI: 10.5151/chempro-14bmos-R0372-1

Referências bibliográficas

• [1] 1 (a) Ali, A. M.; Mackeen, M. M.; Hamid, M.; Aun, Q. B.; Zauyah, H.; Azimathol, H. L. P.; Kawazu, K. Planta Med. 1997, 63, 81; (b) Pihie, A. H. L.; Stanslas, J.; Bin, D. L. Anticancer Res. 1998, 18, 1739. 2 Virolleaud, M. -A.; Bressy, C.; Piva, O. Tet. Lett. 2003, 44, 8084.

Como citar:

Bruder, Marjorie; Pilli, Ronaldo Aloise; "A tandem ring-closing/cross-coupling metathesis reaction toward the short synthesis of goniothalamin analogs", p-372-372. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0372-1