Abstract A mild and general method for the synthesis of dimethylallyl tryptophan derivatives 11 and 12 is described. Reaction of the 3-(γ, γ-dimethyl-allyl) indoles 7a or 7b with the nitroso olefin 8 yields the cycloadducts 9a (93%) and 9b (87%), respectively. Subsequent treatment of 9a with trifluoroacetic acid affords the 2-(dimethylallyl) tryptophan derivatives 11a and 12a in a 9: 1 ratio (97% yield). Isomerisation of 9b gave only 11b (88% yield).
