81763-39-5

Upstream product

• 17791-32-1 7-Oxabicyclo<2.2.1>hept-5-en-2-carbonsaeure-methylester 
• 21987-33-7 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid,methyl ester 
• 24363-23-3 (+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid 
• 17791-32-1 exo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 

Downstream Products

• 90049-70-0 (1R,2R,4S,5S,6R)-1-(3,8-Dioxa-tricyclo[3.2.1.0^2,4]oct-6-yl)-methanol 
• 117714-33-7 DL-(1,2,4/3,6)-1,2-di-O-acetyl-3,6-dibromo-4-bromomethyl-cyclohexane 
• 117693-36-4 DL-(1,2,4/3,6)-4-acetoxymethyl-1,2-di-O-acetyl-3,6-dibromo-1,2-cyclohexanediol 
• 90687-25-5 3-hydroxy-6-methoxycarbonyl-7-oxa-tricyclo<2.2.1.0^2,6>heptane 
• 90687-25-5 (1S,2S,4S,5R,6R)-5-Hydroxy-3-oxa-tricyclo[2.2.1.0^2,6]heptane-1-carboxylic acid methyl ester 
• 78844-86-7 methyl cis-3,4-epoxy-5-hydroxy-cyclohexene-1-carboxylate 

Relevant academic research and scientific papers

BRIEF SYNTHESES OF (+/-)-METHYL SHIKIMATE, (+/-)-METHYL EPISHIKIMATE AND STRUCTURAL VARIANTS

Two brief syntheses of (+/-)-methyl shikimate are described in a strategy which offers potentially flexible access to a range of analogues.New intramolecular rearrangement reactions of epoxides derived from methyl 7-oxabicyclohept-3-ene 6-carboxylate and methyl bicyclohept-3-ene 6 carboxylate are described.

COMPLEMENTARY SHORT SYNTHESES OF (+/-)-METHYL SHIKIMATE

Two syntheses of (+/-)-methyl shikimate from the adduct of furan and methyl acrylate are described.One requires the regioselective hydroxylation of (+/-)-5β,6β-dihydroxy-O,O-isopropylidene-2-methoxycarbonylcyclohexa-1,3-diene and the other cis-dihydroxyla

SHIKIMIC ACIDS FROM FURAN; METHODS OF STEREOCONTROLLED ACCESS TO 3,4,5-TRIOXIGENATED CYCLOHEXENES

Oxabicycloheptenes 1 and 2 are converted to 3,4,5-oxigenated cyclohexenes by stereocontrolled hydroxylations and epoxidations coupled with reverse-Michael cleavage of the oxabicyclo system.Three epimers of shikimic acid are synthesized by these methods.