61414-72-0

Upstream product

• 80631-86-3 (3S,4R,5R)-4-Hydroxy-3-(1-methoxycarbonyl-vinyloxy)-5-phenylselanyl-cyclohex-1-enecarboxylic acid methyl ester 
• 86863-49-2 methyl (1β,6β)-2β--7-oxabicyclo<4.1.0>hept-3-ene-4-carboxylate 
• 80631-85-2 methyl (1β,5α,6β)-5-<<1-(methoxycarbonyl)ethenyl>oxy>-7-oxabicyclo<4.1.0>hept-3-ene-3-carboxylate 
• 76947-23-4 methyl (1β,6β)-2β-hydroxy-7-oxabicyclo<4.1.0>hept-3-ene-4-carboxylate 
• 76947-26-7 (1S,2S,4S,7S)-3,8-Dioxa-tricyclo[5.1.0.0^2,4]octane-5-carboxylic acid methyl ester 
• 6493-77-2 methyl cyclohex-3-ene-1-carboxylate 
• 86863-50-5 (3β,4α,5β)-3-<(1-carboxyethenyl)oxy>-4-hydroxy-5-(phenylseleno)-1-cyclohexene-1-carboxylic acid 
• 186581-53-3 diazomethane 
• 80657-95-0 chorismic acid 
• 96251-69-3 (3R,4R,5R)-3,4-Dihydroxy-5-(1-methoxycarbonyl-vinyloxy)-cyclohex-1-enecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Conversion of Shikimic Acid to 5-Enolpyruvylshikimate 3-Phosphate

The synthesis of (-)-5-enolpyruvylshikimate 3-phosphate (3), a principle metabolite in the shikimic acid pathway, has been accomplished in 22percent overall yield from the known acetonide 6.A key intermediate in the synthesis is diester 9.Direct cyclization of this material affords lactone 10 and distinguishes the three hydroxyl groups of the shikimate nucleus.The phosphate moiety is introduced efficiently with tetrabenzyl pyrophosphate, followed by deprotection with trimethylsilyl bromide. (-)-5-Enolpyruvylshikimic acid (4), a secondary metabolite in the shikimate/chlorismate pathway, is formed on hydrolysis of 9.

IMPROVED SYNTHESIS OF RACEMIC CHORISMIC ACID. CLAISEN REARRANGEMENT OF 4-EPI-CHORISMIC ACID AND DIMETHYL 4-EPI-CHORISMATE.

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.