Synthesis of Disodium 3-cyclohepta-1,6-diene-1-carboxylate: A Seven-Membered Ring Analogue of Chorismate.

Article abstract of DOI:10.1021/jo00252a033

The synthesis of seven-membered ring analogue of chorismate, disodium 3-<(1-carboxylatoethenyl)oxy>-cyclohepta-1,6-diene-1-carboxylate (4c), was accomplished in 3percent overall yield from cycloheptanone.Compound χ was not processed by chorismate mutase, but it was a moderate inhibitor of the normal enzyme-catalyzed conversion of chorismate to prephenate.Prephenate analogue 5c did not inhibit the prephenate dehydrogenase catalyzed decarboxylation of prephenate.Thermolysis of the dimethyl ester 4c led to a complex mixture of products via 1,5-hydrogen migrations, <3,3> Claisen rearrangement, and intramolecular Michael and Diels-Alder reactio n.The products were separated and identified on the basis of spectral and analytical data.