Tetrahedron Letters p. 3755 - 3758 (1986)
Update date:2022-08-17
Topics:
Plate, Ralf
Ottenheijm, Harry C. J.
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 percent) and 9b (87percent), respectively.Subsequent treatment of 9a with trifluoroacetic acid affords the 2-(dimethylallyl) tryiptophan derivatives 11a and 12a in a 9:1 ratio (97 percent yield).Isomerisation of 9b gave only 11b (87 percent yield).
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(1986)Doi:10.1039/c8cc03430c
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