156487-75-1

Upstream product

• 80245-51-8 4-lithio-1,2-dimethoxybenzene 
• 71117-41-4 methyl 4,6-O-benzylidene-α-D-altropyranoside 
• 156487-70-6 Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester 
• 156487-71-7 Benzoic acid (3S,4R,5S,6S)-6-methoxy-4,5-bis-methoxymethoxy-2-methylene-tetrahydro-pyran-3-yl ester 
• 187277-49-2 Benzoic acid (1S,2S,3R)-4-hydroxy-2,3-bis-methoxymethoxy-6-oxo-cyclohexyl ester 
• 156487-72-8 Benzoic acid (1S,5R,6S)-5,6-bis-methoxymethoxy-2-oxo-cyclohex-3-enyl ester 
• 156487-73-9 1L-<1(OH),2,3/4>-3,4-Bis-O-(methoxymethyl)-1-(3,4-dimethoxyphenyl)cyclohex-5-ene-1,2,3,4-tetrol 
• 156487-69-3 Methyl 4,6-O-benzylidene-2,3-bis-O-(methoxymethyl)-α-D-altropyranoside 
• 156726-58-8 1L-<1(OH),2,3/4>-3,4-Bis-O-(methoxymethyl)-1-(3,4-dimethoxyphenyl)cyclohexane-1,2,3,4-tetrol 
• 156487-74-0 (1S,4R,5S,6S)-4,5-Bis(methoxymethoxy)-1-(3,4-dimethoxyphenyl)-7,9-dioxabicyclo<4.3.0>nonane-8-thione 

Downstream Products

• 156558-40-6 (3S,4R)-1-(3,4-Dimethoxyphenyl)-3-hydroxy-4-(methoxymethoxy)cyclohexene 
• 156487-77-3 (3R,4R)-1-(3,4-Dimethoxyphenyl)-3-hydroxy-4-(methoxymethoxy)cyclohexene 
• 156487-79-5 2-<(1R,4R)-1-(3,4-Dimethoxyphenyl)-4-(methoxymethoxy)cyclohex-2-enyl>ethanal 
• 156487-80-8 N-<2-<(1R,4R)-1-(3,4-Dimethoxyphenyl)-4-(methoxymethoxy)cyclohex-2-enyl>>ethyl-N-methylamine 
• 156487-81-9 O-Methoxymethyl mesembranol 
• 156487-78-4 Ethyl <(1R,4R)-1-(3,4-dimethoxyphenyl)-4-(methoxymethoxy)cyclohex-2-enyl>acetate 
• 23544-42-5 (-)-Mesembranol 

Relevant academic research and scientific papers

Chiral and stereoselective total synthesis of (-)-mesembranol starting from D-glucose

A chiral synthesis of the Sceletium alkaloid (-)-mesembranol 1 is described. The cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation, and the critical stereochemistry of the quaternary carbon in 1 is constructed stereoselectively via chirality transfer by way of Claisen rearrangement of the cyclohexenol derivative 14a. The perhydroindole skeleton in 1 is effectively generated by intramolecular aminomercuriation of the amino-olefin 18.

Chiral synthesis of (-)-mesembranol starting from D-glucose

The chiral synthesis of the Sceletium alkaloid, (-)-mesembranol 1 is described; the cyclohexane ring in 1 is prepared in an optically active form from D-glucose using Ferrier's carbocyclisation reaction and the perhydroindole skeleton is effectively constructed by an intramolecular aminomercuration reaction.