247227-98-1

Upstream product

• 67-56-1 methanol 
• 74219-29-7 (1'S,2'S)-5'-methyl-4-pentyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol 
• 112639-16-4 2-iodo-1,3-dimethoxy-5-pentylbenzene 

Downstream Products

• 33029-18-4 Δ⁹-tetrahydrocannabinol 
• 847949-34-2 (3S,4S)-3-(2,6-Diacetoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enecarboxylic acid 
• 847949-32-0 Acetic acid 3-acetoxy-2-((1S,6S)-3-bromomethyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester 
• 847949-33-1 Acetic acid 3-acetoxy-2-((1S,6S)-3-formyl-6-isopropenyl-cyclohex-2-enyl)-5-pentyl-phenyl ester 
• 847949-28-4 Acetic acid (3S,4S)-3-(2,6-dimethoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enylmethyl ester 
• 847949-29-5 [(3S,4S)-3-(2,6-Dimethoxy-4-pentyl-phenyl)-4-isopropenyl-cyclohex-1-enyl]-methanol 
• 847949-27-3 2-((1S,6S)-3-Bromomethyl-6-isopropenyl-cyclohex-2-enyl)-1,3-dimethoxy-5-pentyl-benzene 
• 847949-24-0 (1R,4S,5S,6S)-5-(2,6-Dimethoxy-4-pentyl-phenyl)-4-isopropenyl-1-methyl-7-oxa-bicyclo[4.1.0]heptane 

Relevant academic research and scientific papers

Short and Divergent Total Synthesis of (+)-Machaeriol B, (+)-Machaeriol D, (+)-Δ8-THC, and Analogues

Short and highly efficient stereoselective syntheses provide machaeriols and cannabinoids in a divergent approach starting from a common precursor, commercially available (S)-perillic acid. Key features of the novel strategy are a stereospecific palladium-catalyzed decarboxylative arylation and a one-pot sequence comprising a stereoselective hydroboration followed by oxidation or reduction of the corresponding intermediary boranes. The divergent approach is convincingly demonstrated by the five-step syntheses of (+)-machaeriol B, (+)-machaeriol D, and related analogues, and the four-step synthesis of (+)-Δ8-THC and an analogue.

Enantiomeric cannabidiol derivatives: Synthesis and binding to cannabinoid receptors

(-)-Cannabidiol (CBD) is a major, non psychotropic constituent of cannabis. It has been shown to cause numerous physiological effects of therapeutic importance. We have reported that CBD derivatives in both enantiomeric series are of pharmaceutical interest. Here we describe the syntheses of the major CBD metabolites, (-)-7-hydroxy-CBD and (-)-CBD-7-oic acid and their dimethylheptyl (DMH) homologs, as well as of the corresponding compounds in the enantiomeric (+)-CBD series. The starting materials were the respective CBD enantiomers and their DMH homologs. The binding of these compounds to the CB1 and CB2 cannabinoid receptors are compared. Surprisingly, contrary to the compounds in the (-) series, which do not bind to the receptors, most of the derivatives in the (+) series bind to the CB1 receptor in the low nanomole range. Some of these compounds also bind weakly to the CB2 receptor. The Royal Society of Chemistry 2005.