New approach for the construction of the coumarin frame and application in the total synthesis of natural products

…, LE Montiel, F Delgado, J Tamariz

Index: Jerezano, Alberto; Jimenez, Fabiola; Del Carmen Cruz, Maria; Montiel, Luisa E.; Delgado, Francisco; Tamariz, Joaquin Helvetica Chimica Acta, 2011 , vol. 94, # 2 p. 185 - 198

Full Text: HTML

Citation Number: 17

Abstract

Abstract A new synthetic approach is described for building the coumarin scaffold through the Lewis acid-promoted cyclization of novel aryl 3-(dimethylamino) prop-2-enoates 2a–2f. The latter precursors were prepared via aminomethylenation of the corresponding aryl acetates 4a–4f with the Bredereck reagent. This approach was used for the synthesis of biologically active natural compounds 1a–1f, through a three-step procedure starting from ...

Related Articles:

Yb (OTf) 3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: one-pot assembly of 3, 4-dihydrocoumarins, 4-chromanones, coumarins, and chromones

[Fillion, Eric; Dumas, Aaron M.; Kuropatwa, Bryan A.; Malhotra, Neil R.; Sitler, Tamsyn C. Journal of Organic Chemistry, 2006 , vol. 71, # 1 p. 409 - 412]

Two-photon uncaging with fluorescence reporting: evaluation of the o-hydroxycinnamic platform

[Gagey, Nathalie; Neveu, Pierre; Benbrahim, Chouaha; Goetz, Bernard; Aujard, Isabelle; Baudin, Jean-Bernard; Jullien, Ludovic Journal of the American Chemical Society, 2007 , vol. 129, # 32 p. 9986 - 9998]

Toward establishing structure–activity relationships for oxygenated coumarins as differentiation inducers of promonocytic leukemic cells

[Riveiro, Maria E.; Maes, Dominick; Vazquez, Ramiro; Vermeulen, Monica; Mangelinckx, Sven; Jacobs, Jan; Debenedetti, Silvia; Shayo, Carina; De Kimpe, Norbert; Davio, Carlos Bioorganic and Medicinal Chemistry, 2009 , vol. 17, # 18 p. 6547 - 6559]

Synthesis of coumarins by ring-closing metathesis using Grubbs' catalyst

[Nguyen Van, Tuyen; Debenedetti, Silvia; De Kimpe, Norbert Tetrahedron Letters, 2003 , vol. 44, # 22 p. 4199 - 4201]

Synthesis of coumarins by ring-closing metathesis using Grubbs' catalyst

[Nguyen Van, Tuyen; Debenedetti, Silvia; De Kimpe, Norbert Tetrahedron Letters, 2003 , vol. 44, # 22 p. 4199 - 4201]

More Articles...