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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