78844-86-7

Upstream product

• 108-05-4 vinyl acetate 
• 78844-86-7 rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol 
• 141318-30-1 (1R,4R,5R,6R,8S)-5-iodo-3,7-dioxatricyclo<4.2.1.0_4,8>nonan-2-one 
• 84752-05-6 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride 
• 3409-31-2 methyl cis-4,5-diacetoxy-cyclohexene-1-carboxylate 
• 83604-10-8 rac-methyl 5-hydroxycyclohexa-1,3-diene-1-carboxylate 
• 90687-26-6 (+/-)-methyl-5-β-O-t-butyldimethylsilyloxycyclohexa-1,3-dienoate 
• 83604-09-5 methyl 7-oxabicyclo<4.1.0>hept-3-ene-3-carboxylate 
• 89678-08-0 rac-(1R,2R,3R,6R,7S)-2-iodo-4,8-dioxatricyclo[4.2.1.0^3,7]nonan-5-one 
• 74-88-4 methyl iodide 
• 78844-89-0 methyl 3-deoxyshikimate 
• 50983-21-6 1,4-Cyclohexadien-1-carbonsaeure-methylester 
• 17791-32-1 7-Oxabicyclo<2.2.1>hept-5-en-2-carbonsaeure-methylester 
• 81763-39-5 exo-2,3-epoxy-6-methoxycarbonyl-7-oxabicyclo<2.2.1>heptane 

Downstream Products

• 106861-60-3 (-)-methyl (1β,2β,6β)-2-hydroxy-7-oxabicyclo<4,1,0>hept-3-ene-4-carboxylate 
• 130575-47-2 (3S,4S,5R)-4,5-Dihydroxy-3-methoxy-cyclohex-1-enecarboxylic acid methyl ester 
• 171963-37-4 3(S),4(S),5(R)-trihydroxy-1-cyclohexene-1-carboxylic acid 
• 175546-00-6 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylic acid 
• 494195-98-1 (1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene 
• 635678-66-9 (2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one 
• 635678-63-6 (1R,2S,4S,5R,7R)-7-hydroxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octan-5-ol 
• 4372-89-8 methyl (3R*,4R*,5S*)-3,4,5-trihydroxy-1-cyclohexenecarboxylate 
• 635678-67-0 RKTS-34 
• 80631-83-0 2-((1R,5S,6S)-6-Benzoyloxy-5-bromo-3-methoxycarbonyl-cyclohex-2-enyloxy)-2-dimethylaminomethyl-malonic acid dimethyl ester 
• 80631-80-7 methyl (1α,5α,6α)-5--8-phenyl-7,9-dioxabicyclo<4.3.0>non-3-ene-3-carboxylate 
• 80631-79-4 2-Hydroxy-2-((3aR,4R,7aR)-6-methoxycarbonyl-2-phenyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-malonic acid dimethyl ester 
• 80631-82-9 methyl (3β,4α,5β)-3--4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 
• 80631-84-1 methyl (3β,4α,5β)-3-<<1-(methoxycarbonyl)ethenyl>oxy>-4-(benzoyloxy)-5-bromo-1-cyclohexene-1-carboxylate 

Relevant academic research and scientific papers

Total synthesis of epoxyquinols A, B, and C and epoxytwinol A and the reactivity of a 2H-pyran derivative as the diene component in the Diels-Alder reaction

(Chemical Equation Presented). Full details of two versions of the total synthesis of epoxyquinols A, B, and C and epoxytwinol A (RKB-3564D) are described. In the first-generation synthesis, the HfCL4-mediated diastereoselective Diels-Alder rea

Novel non-peptide inhibitors targeting death receptor-mediated apoptosis

We have previously reported that ECH, (2R, 3R, 4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-6-(1E)-propenyl-cyclohex-5-en-1-one inhibits Fas-mediated apoptosis by blocking self-activation of pro-caspase-8 in the death-inducing signaling complex (DISC). A series of ECH derivatives were asymmetrically synthesized via key synthetic intermediates obtained from lipase-catalyzed kinetic resolution. Inhibitory activities of the derivatives towards death receptor-mediated apoptosis both in type I and type II cells were investigated, revealing that novel non-peptide inhibitors, RKTS-33 and RKTS-34, are effective as ECH.

A practical total synthesis of both enantiomers of epoxyquinols A and B

A practical total synthesis of both enantiomers of epoxyquinols A and B has been developed. Key reactions are the chromatography-free preparation of an iodolactone by using acryloyl chloride as dienophile in the Diels-Alder reaction of furan, the lipase-mediated kinetic resolution of a cyclohexenol derivative, and a modified procedure for α-iodonation of a cyclohexenone.

Total synthesis of (+)-epoxyquinols A and B

A highly stereoselective HfCl4-mediated Diels-Alder reaction of furan and the chiral acrylate ester of Corey's auxiliary to subsequently give 1, and the realization of the postulated biosynthetic pathway for the construction of epoxyquinols A a

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.

Synthesis of (-)-3(R)-amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid: The 3(R)-amino analogue of (-)-shikimic acid

(-)-3(R)-Amino-4(R),5(R)-dihydroxy-1-cyclohexene-1-carboxylic acid (the 3(R)-amino analogue of (-)-shikimic acid) has been synthesised from (-)-shikimic acid in seven steps. Copyright

ON THE STRUCTURE OF NATURALLY-OCCURRING (+)-METHYL 3,4-ANHYDROSHIKIMATE

A two-step synthesis of enantiomerically pure (+)-methyl 3,4-anhydroshikimate 2 from (-)- methyl shikimate 3 is described, leading to a revision in the properties reported for this natural product.

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.