53399-74-9

Upstream product

• 917-64-6 methyl magnesium iodide 
• 2158-59-0 cryptone 
• 112068-28-7 (3R,4R)-1-methyl-4-(1-methylethyl)-cyclohex-1-en-3-yl acetate 
• 913548-06-8 (1R,2R,4S)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol 
• 2158-59-0 (R)-(-)-cryptone 
• 917-54-4 methyllithium 
• 579473-51-1 (-)-carvomethene epoxide 
• 5989-54-8 (-)-(S)-limonene 
• 499-94-5 (S)-carvomenthene 
• 913548-03-5 (4S)-1-tert-butyldimethylsilyloxymethyl-1,2-epoxy-4-isopropylcyclohexane 
• 913548-05-7 (4S)-1-hydroxymethyl-4-isopropyl-2-phenylselenenylcyclohexan-1-ol 
• 913548-04-6 (4S)-1-tert-butyldimethylsilyloxymethyl-4-isopropyl-2-phenylselenenylcyclohexan-1-ol 
• 536-59-4 (-)-perillyl alcohol 
• 863880-06-2 (R)-2-isopropyl-5-carbonylhexanal 

Downstream Products

• 877660-90-7 (-)-(1'S,2'S)-2'-isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol 

Relevant academic research and scientific papers

Method for synthesizing bark beetle pheromone

The bark beetle pheromone is (1S, 4R) -4 - isopropyl -1 - methyl -2 -cyclohexene -1 - alcohol, and the synthetic method comprises the following steps: forming a clathrate compound with (S)- (-) - limonene and carrying out catalytic hydrogenation reaction

PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF

The present invention relates to process for the preparation of cannabidiol (A) from the coupling of (D) and (E) through the intermediates (C) and (D) starting from compound (B). The invention further relates to the novel compounds (B), (C), (D) and (E) and reagents used in this process. More specifically, this invention provides the manufacturing of Cannabidiol (A) in milligram to gram or kilogram scale.

Enantioselective biomimetic total syntheses of katsumadain and katsumadain C

Enantioselective total syntheses of katsumadain and katsumadain C were achieved concisely through a biomimetic approach. Assembly of styryl-2-pyranone (3) and monoterpene 6 via acid-promoted regio- and stereoselective C-C bond formation afforded katsumada

A new diastereoselective entry to the (1S,4R)- and (1S,4S)-isomers of 4-isopropyl-1-methyl-2-cyclohexen-1-ol, aggregation pheromones of the ambrosia beetle Platypus quercivorus

A concise diastereoselective and enantiopure route to the (1S,4R)- and (1S, 4S)-isomers of 4-isopropyl-1-methyl-2-cyclohexen-1-ol via a palladium-catalysed deoxygenation of the enol triflate derived from limonene glycol. Crown Copyright

Determination of the absolute configuration of quercivorol, (1S,4R)-p-menth-2-en-1-ol, an aggregation pheromone of the ambrosia beetle Platypus quercivorus (Coleoptera: Platypodidae)

A pair of enantiomers of trans-p-menth-2-en-1-ol, an aggregation pheromone of Platypus quercivorus, was synthesized from (S)- and (R)-limonene. The retention time of the aggregation pheromone from the insect coincided with that of (1S,4R)-p-menth-2-en-1-ol synthesized from (S)-limonene from GC analyses with a chiral column, enabling the absolute configuration of the aggregation pheromone to be determined as (1S,4R).

Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

(S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (±)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide.

Microbial Allyl Rearrangement and Resolution of Acetates of Unsaturated Cyclic Terpene Alcohols by Pseudomonas sp. NOF-5 Strain

Microbial hydrolysis of the acetates of unsaturated cyclic terpene alcohols by Pseudomonas sp.NOF-5 isolated from soil was investigated. (+/-)-trans-Carveyl acetate ((+/-)-trans-3) was enantioselectively hydrolyzed with NOF-5 strain to give (-)-trans-carveol ((-)-trans-2 of 86.6percent optical purity).However, the hydrolysis of (+/-)-cis-3 was less enantioselective, while (+/-)-piperitylacetate ((+/-)-6, a cis and trans mixture) was hydrolyzed to give the (-)-trans- and (-)-cis-piperitols ((-)-trans-5 and (-)-cis-5) in a poor optical yield.In this case, other tert-alcohols, (+)-trans- and (-)-cis-2-p-menthen-1-ols ((+/-)-trans-7 and (-)-cis-7, were also produced.Furthermore, microbial and enzymic allyl rearrangements of (+)-trans-6 and (-)-trans-verbenylacetate ((-)-trans-11) were studied.Biological treatment of (+)-trans-6 and (-)-trans-11 with NOF-5 or its esterase gave (+)-trans- and (-)-cis-7 and (+)-cis-3-pinen-2-ol ((+)-cis-12), respectively.