The gold-catalysed double functionalisation of indoles is presented. Enynones are used to annulate indoles via a double sodium tetrachloroaurate-catalysed process involving a mixture of C À H activation and alkyne activation modes of promo-tion. Good yields for the formation of medicinally relevant [6,5,7]-tricyclic indoles are realised.
A tandem double Friedel-Crafts reaction of indoles and nonsymmetrical divinyl ketones has been achieved. The tandem reaction forms complex [6-5-7]-tricyclic indoles in excellent yields. The reaction is completely regioselective and offers high levels of syn diastereoselectivity. The reaction is also seen to be sensitive to substrate structure and catalyst.
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