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Palladium-Catalyzed Oxyarylation, Azaarylation and α-Arylation Reactions in the Synthesis of Bioactive Isoflavonoid Analogues

[ Vol. 12 , Issue. 6 ]

Author(s):

Camilla D. Buarque, Jorge L. O. Domingos, Chaquip D. Netto and Paulo R. R. Costa   Pages 772 - 794 ( 23 )

Abstract:


Isoflavonoids constitute an important class of natural products, comprising great structural diversity. Known as phytoalexins and phytoestrogens, these compounds exhibit interesting biological activities. The corresponding carba-analogues, in which the oxygen atom at the B-ring is replaced by a methylene, are emerging as an attractive alternative for the preparation of new bioactive compounds. In this review, we report our results on the synthesis of isoflavonoid analogues (5-carba-pterocarpans, 1-carba-isoflavanones, 5-carba-11-aza-pterocarpan and pterocarpanquinones) with anti-cancer, antiparasitic and anti-viral properties. Palladium-catalyzed oxyarylation and azaarylation of dihydronaphthalenes and α-arylation of α- tetralones were the key steps in the developed synthetic approaches. A historical background, as well as a brief mechanistic discussion of these reactions, will be presented.

Keywords:

Isoflavonoids, Carba-isoflavonoids, Oxyarylation, Azaarylation, α-Arylation, Palladium-catalyzed.

Affiliation:

Department of Chemistry, Pontifical Catholic University of Rio de Janeiro University, P.O. Box: 22451-900, Rio de Janeiro, Brazil.

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