Journal of the American Chemical Society p. 6264 - 6267 (1983)
Update date:2022-07-31
Topics:
Hoare
Policastro
Berchtold
The total synthesis of racemic chorismic acid (1) in eleven steps (6% overall yield) from methyl cyclohex-1-ene-4-carboxylate (9) is described. Dimethyl 4-epi-chorismate (8) and 4-epi-chorismic acid (6) are prepared by similar procedures, and their rate of Claisen rearrangement is investigated. A convenient preparation of disodium prephenate (2) and disodium 4-epi-prephenate (5) from dimethyl chorismate (7) and 8, respectively, is described.
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