Total synthesis of the pyranoisoflavone kraussianone 1 and related isoflavones.
The first total synthesis of the pyranoisoflavone kraussianone 1 (1) is described. The key steps involved the Suzuki-Miyaura reaction for the construction of the isoflavone core and the regioselective formation of the dimethylpyran scaffolds to the phloroglucinol (ring A) and resorcinol (ring B) moieties of kraussianone 1 (1). This route also provided access to the related isoflavones eriosemaone D (2) and genistein (3) via simple structural modifications.
Selepe
Mamoalosi A
MA
School of Chemistry, University of KwaZulu-Natal, Private Bag X01, Scottsville 3209, Pietermaritzburg, South Africa.
Drewes
Siegfried E
SE
van Heerden
Fanie R
FR
D007887:Fabaceae / Q000737:chemistry; D019833:Genistein / Q000737:chemistry; D007529:Isoflavones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry
D007529:Isoflavones; C000605895:eriosemaone D; C465002:kraussianone 1; D019833:Genistein