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Vinylpyrrolo-[2,1-a]-β-carbolines 1 give different products upon reaction with dienophiles. With dimethyl acetylenedicarboxylate (DMAD), a novel domino process takes place, involving Michael attack and rearrangement, affording complex polycycles like 3, 4, and 5. Diels–Alder cycloadditions are favored in the presence of Lewis acids and are the only reactions with dimethyl maleate. When 3-butyn-2-one...
The RCM metathesis reaction catalyzed by Grubbs’ ruthenium catalyst is used with a series of 1,2-disubstituted indoles leading with excellent yields to tricyclic compounds. When applied to 1-allyl-2-vinylindoles this methodology allows a new entry to the mitosene skeleton.
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