A Rapid Assembly of Furo[3,4-b]-and Pyrrolo[3,4-b]carbazolones by DominoWittig Diels-Alder Reaction. -Reaction of indolecarboxaldehydes (I) and (V) with phosphoranes (II) provides regioisomeric lactones as mixtures of cis-and trans-isomers. The following oxidation with DDQ yields the corresponding carbazoles. -(TORNEY, P.; PATRE, R.; TILVE*, S.; Synlett 2011, 5, 639-642, http://dx.doi.org/10.1055/s-0030-1259695 ; Dep. Chem., Goa Univ., Goa 403 206, India; Eng.) -Mais 26-123
A new method for the synthesis of the indolocarbazole alkaloid arcyriaflavin A is described. The synthetic strategy employs a graphite-catalysed alkenation, one-pot oxidation-Wittig reaction, iodine-catalysed electrocyclisation and nitrene insertion as the key steps. The strategy also constitutes a formal synthesis of another indolocarbazole alkaloid staurosporinone.
A convenient two step protocol for the synthesis of carbazole lignans involving domino Wittig reaction/Diels—Alder reaction followed by aromatization with DDQ is described.
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