80631-86-3Relevant articles and documents
IMPROVED SYNTHESIS OF RACEMIC CHORISMIC ACID. CLAISEN REARRANGEMENT OF 4-EPI-CHORISMIC ACID AND DIMETHYL 4-EPI-CHORISMATE.
Hoare,Policastro,Berchtold
, p. 6264 - 6267 (2007/10/02)
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.