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

Author(s): Camilla D. Buarque, Jorge L. O. Domingos, Chaquip D. Netto, Paulo R. R. Costa

Journal Name: Current Organic Synthesis

Volume 12 , Issue 6 , 2015

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Graphical 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.

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Article Details

Year: 2015
Page: [772 - 794]
Pages: 23
DOI: 10.2174/157017941206150828112502
Price: $65

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