619335-64-7

Upstream product

• 100-39-0 benzyl bromide 
• 619335-73-8 (2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)methanol 
• 474956-28-0 6-allyl-6-methyl-1,4,8,11-tetraoxadispiro[4.1.4.3]tetradecane 
• 31929-07-4 2-allyl-2-methyl-1,3-cyclohexanedione 
• 856177-30-5 (E)-6-methyl-6-(1-propen-1-yl)-1,4,8,11-tetraoxadispiro[4.1.4.3]tetradecane 
• 856177-34-9 (6-methyl-1,4,8,11-tetraoxadispiro[4.1.4.3]tetradec-6-yl)methanol 
• 856177-38-3 6-benzyloxymethyl-6-methyl-1,4,8,11-tetraoxadispiro[4.1.4.3]tetradecane 
• 619335-65-8 {[(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)methoxy]methyl}benzene 
• 82939-66-0 methyl 2,6-dimethoxy-2,5-cyclohexadiene-1-carboxylate 
• 82478-17-9 methyl 2,6-dimethoxy-1-methylcyclohexa-2,5-diene-1-carboxylate 

Downstream Products

• 619335-62-5 (2R,3S)-2-Benzyloxymethyl-3-hydroxy-2-methyl-cyclohexanone 
• 619335-63-6 (1S,3S)-2-benzyloxymethyl-2-methylcyclohexane-1,3-diol 
• 856178-52-4 (2R,4aS,8aS)-hexahydro-4a-methyl-2-phenylbenzo[d][1,3]dioxin-5-one 
• 856178-55-7 (Z,2R,4aS,9aS)-4,4a,9,9a-tetrahydro-4a-methyl-2-phenylcyclohepta[d][1,3]dioxin-5(8H)-one 
• 619335-74-9 (1S,3S)-2-hydroxymethyl-2-methylcyclohexane-1,3-diol 
• 619335-75-0 (2R,3S)-3-hydroxy-2-hydroxymethyl-2-methylcyclohexanone 
• 619335-66-9 (2R,4aR,5S,8aS)-hexahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-5-ol 
• 619335-76-1 (1S,2S,3S)-3-benzyloxy-2-hydroxymethyl-2-methylcyclohexanol 
• 619335-71-6 (4aR,5S,8aS)-5-benzyloxy-hexahydro-2,2,4a-trimethylbenzo[d][1,3]dioxine 
• 815577-89-0 (2R,4aR,8aS)-4a,7,8,8a-tetrahydro-5-iodo-4a-methyl-1-phenyl-4H-benzo[d][1,3]dioxine 
• 815578-00-8 ((1R,6S)-6-(benzyloxy)-2-iodo-1-methylcyclohex-2-enyl)methanol 

Relevant academic research and scientific papers

Formal total synthesis of (-)-taxol through Pd-catalyzed eight-membered carbocyclic ring formation

A formal total synthesis of (-)-taxol by a convergent approach utilizing Pd-catalyzed intramolecular alkenylation is described. Formation of the eight-membered carbocyclic ring has been a problem in the convergent total synthesis of taxol but it was solved by the Pd-catalyzed intramolecular alkenylation of a methyl ketone affording the cyclized product in excellent yield (97 %), indicating the high efficiency of the Pd-catalyzed intramolecular alkenylation. Rearrangement of the epoxy benzyl ether through a 1,5-hydride shift, generating the C3 stereogenic center and subsequently forming the C1-C2 benzylidene, was discovered and utilized in the preparation of a substrate for the Pd-catalyzed reaction.

Preparation of new chiral building blocks: Highly enantioselective reduction of prochiral 1,3-cycloalkanediones possessing a methyl group and a protected hydroxymethyl group at their C2 position with Baker's yeast or CBS catalyst

Highly enantioselective reduction of five-, six-, seven-, and eight-membered prochiral 1,3-cycloalkanediones possessing a methyl group and a protected hydroxymethyl group at their C2 position with baker's yeast or CBS catalyst and a new efficient and general method for preparing the 1,3-cycloalkanediones have been developed. These baker's yeast mediated reductions were found to produce corresponding ketols with high optical purity (> 99% ee) and high yield. All of the prepared ketols and their derivatives, chiral building blocks, have been fully characterized, and their absolute configurations have been determined. These compounds would be useful for the convergent synthesis of complex natural products.

Preparation of new chiral building blocks via asymmetric catalysis

Highly enantio- and stereoselective preparation of some new chiral building blocks with baker's yeast or the CBS catalyst is described.