171963-37-4

Upstream product

• 1476028-68-8 (3R,4S,5R)-ethyl 3,4-epoxy-5-hydroxycyclohex-1-ene-1-carboxylate 
• 179738-33-1 Benzoic acid (1S,2S,6R)-2-bromo-6-hydroxy-4-methoxycarbonyl-cyclohex-3-enyl ester 
• 179738-32-0 Benzoic acid (1S,2S,6R)-2-chloro-6-hydroxy-4-methoxycarbonyl-cyclohex-3-enyl ester 
• 179738-34-2 (1R,5R,6S)-5-Benzoyloxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester 
• 78844-86-7 methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate 
• 40983-58-2 methyl shikimate 
• 175546-00-6 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylic acid 
• 171963-38-5 methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate 
• 138-59-0 shikimic acid 

Downstream Products

• 171963-38-5 methyl [3S-(3α,4β,5α)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate 

Relevant academic research and scientific papers

Stereodivergent Syntheses of All Stereoisomers of (?)-Shikimic Acid: Development of a Chiral Pool for the Diverse Polyhydroxy-cyclohexenoid (or -cyclohexanoid) Bioactive Molecules

Novel stereodivergent total syntheses of all the seven stereoisomers of (?)-shikimic acid [(?)-SA 1] have been systematically performed. (+)-ent-SA ent-1 was synthesized from (?)-SA 1 via 9 steps in 31 % overall yield; (?)-3-epi-SA 2 was synthesized from (?)-SA 1 via 5 steps in 66 % overall yield; (+)-3-epi-ent-SA ent-2 was synthesized from (?)-SA 1 via 7 steps in 43 % overall yield; (?)-4-epi-SA 3 was synthesized from (?)-SA 1 via 11 steps in 32 % overall yield; (+)-4-epi-ent-SA ent-3 was synthesized from (?)-SA 1 via 7 steps in 42 % overall yield; (?)-5-epi-SA 4 was synthesized from (?)-SA 1 via 6 steps in 56 % overall yield; and (+)-5-epi-ent-SA ent-4 was synthesized from (?)-SA 1 via 12 steps in 29 % overall yield. The stereochemistry of all the above seven stereoisomers of (?)-SA 1 were further studied by two dimensional (2D) 1H NMR technique.

Enzyme-catalyzed resolution of 3,8-dioxatricyclo[3.2.1.02,4]octane-6-carboxylic esters and the application to the synthesis of 3-epishikimic acid

3,8-Dioxatricyclo[3.2.1.02,4]octane-6-carboxylic acid, whose racemic form is readily available on a large scale, is a versatile starting material for the synthesis of carbasugars and carbocyclic biologically active natural products. In this stu

Arene cis-dihydrodiols-useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid

The synthesis of 6,6-difluoroshikimic acid (11) has been achieved in ten steps from the enantiopure diol 16, which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid (5).

Benzene-free synthesis of phenol

Heating shikimic acid in near-critical water leads to the formation of phenol. Since shikimic acid can now be obtained by the microbial conversion of glucose, a benzene-freer route to phenol could become an alternative to the industrial Hock oxidation of cumene derived from benzene (see scheme).

Synthesis of (3R)- and (3S)-fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1- carboxylic acids: The (3R)- and (3S)-fluoro analogues of (-)-shikimic acid

(3R)-and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3R)- and (3S)-fluoro analogues of (-)-shikimic acid) have been synthesised from (-)-shikimic acid via an intermediate epoxide (a fungal metabolite from Chalara microspora) that

The shikimate pathway. Part 9. Halogenation at C-3 of the shikimate nucleus

The use of (-)-shikimic acid as starting material in the syntheses of a series of C-3 halogenated derivatives including the analogous 3α- and 3β-fluoro and 3β-chloro acids is described together with the first stereospecific synthesis of (-)-3-epi-shikimic acid directly from the parent acid.