The Journal of Organic Chemistry

Synthesis of disodium 3-[(1-carboxylatoethenyl) oxy] cyclohepta-1, 6-diene-1-carboxylate: A seven-membered ring analog of chorismate

JL Pawlak, GA Berchtold

Index: Pawlak, John L.; Berchtold, Glenn A. Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 4063 - 4069

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Citation Number: 24

Abstract

The synthesis of a seven-membered ring analogue of chorismate, disodium 3-[(1- carboxylatoethenyl) oxy]-cyclohepta-1, 6-diene-l-carboxylate (4c), was accomplished in 3% overall yield from cycloheptanone. Compound 4c 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 ...

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