Synthesis of poinsettifolin A

Zilma Escobar, Carlos Solano, Rikard Larsson, Martin Johansson, Efrain Salamanca, Alberto Gimenez, Eduardo Muñoz, Olov Sterner

Resultado de la investigación: Contribución a una revistaArtículorevisión exhaustiva

10 Citas (Scopus)

Resumen

A synthesis of poinsettifolin A (1), a prenylated flavonol isolated from Dorstenia poinsettifolia, is described. Two routes starting from quercetin were explored, and 1 could be prepared if a prenyl group first was incorporated at C-6 of the protected quercetin followed by a condensation with citral at C-8. The key synthetic steps are a Mitsunobu reaction, an europium (III)-catalysed Claisen rearrangement coupled with cross-metathesis, and a benzopyran-forming geranylation. The two geranylated 3,5,3′,4′-tetrahydroxyflavonols prepared, 1 and 3, were assayed for antileishmanial activity against Leishmania amazonensis and Leishmania braziliensis, and found to be active. Compound 3 showed cytotoxic activity against leukaemia and lung cancer cells while 1 lacked cytotoxicity.

Idioma originalInglés
Páginas (desde-hasta)9052-9056
Número de páginas5
PublicaciónTetrahedron
Volumen70
N.º47
DOI
EstadoPublicada - 25 nov. 2014

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Publisher Copyright:
© 2014 Elsevier Ltd.

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