35408-03-8

Upstream product

• 28239-05-6 (-)-nopinone enol acetate 
• 135503-45-6 (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one 
• 28239-06-7 (+)-cis-3-bromonopinone 
• 546-67-8 lead(IV) tetraacetate 
• 500-66-3 Olivetol 
• 43161-64-4 (+)-(1R,5R)-apopinene 
• 38651-65-9 (1R,5S)-(+)-nopinone 
• 82078-77-1 (+)-6,6-dimethyl-2,2-diacetoxy-3-norpinene 
• 135432-16-5 (1R,3S,5R)-6,6-dimethyl-3-(phenylselanyl)bicyclo[3.1.1]heptan-2-one 
• 18172-67-3 beta-pinene 
• 128301-59-7 (1R,3S,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>heptane-2-one 
• 128261-63-2 (1R,3R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>heptane-2-one 
• 214827-15-3 (1R,3S,5R,R_S)-6,6-dimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one 
• 214827-20-0 (1R,3R,5R,S_S)-6,6-dimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one 

Downstream Products

• 130799-47-2 4-(2-Methoxy-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 122700-14-5 4-(2-Methoxy-4-pentyl-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 122722-23-0 4-(2,6-Bis(methoxymethoxy)-4-pentylphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 149339-38-8 (1R,2R,5R)-2-Benzyl-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-ol 
• 128660-91-3 (+)-4-<4-n-pentyl-2,6-bis(2-ethoxyethyl)phenyl>-6,6-dimethyl-2-norpinanone 
• 54154-44-8 1-methoxy-4-((1R,2R,5R)-5-methyl-2-(prop-1-en-2-yl)-5-vinylcyclohexyl)benzene 
• 138568-27-1 cyclobackuchiol B 
• 130799-43-8 2-(2,6-Dimethoxyphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-ol 
• 132345-24-5 (-)-4-<2,6-Dimethoxy-4-(1,1-dimethylheptyl)phenyl>-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 
• 214827-21-1 (1R,3R,4S,5R,R_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one 
• 214827-18-6 (1R,3R,4S,5R,S_S)-4,6,6-trimethyl-3-(phenylsulfoxy)bicyclo<3.1.1>heptan-2-one 
• 128261-70-1 (1R,3R,4S,5R)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>heptan-2-one 
• 18309-32-5 Verbenone 
• 52691-72-2 (-)-Apoverbenone 

Relevant academic research and scientific papers

Novel C-Ring-Hydroxy-Substituted Controlled Deactivation Cannabinergic Analogues

In pursuit of safer controlled-deactivation cannabinoids with high potency and short duration of action, we report the design, synthesis, and pharmacological evaluation of novel C9- and C11-hydroxy-substituted hexahydrocannabinol (HHC) and tetrahydrocanna

Novel Labelled Cannabinergic Ligands and Related Analogs

Novel cannabinoid ligands represented by the general formulas I, II, and III and methods for preparation and use within which one or more of a fluorescent ligand, nitroxide spin label, metal chelate, biotin moiety, or group with enhanced polarity may be incorporated. The compounds can bind to and modulate the cannabinoid CB1 and CB2 receptors and thereby considered specific ligands for these receptors. Some of the disclosed compounds that bind to cannabinoid CB1 and CB2 receptors can exhibit tight or irreversible binding characteristics for these receptors. Due to the presence of the imaging/diagnostic and/or therapeutic functional groups including fluorescent groups, nitroxide spin labels, metal chelates, biotin moieties, and groups with enhanced polarity, the disclosed compounds may be useful as imaging/diagnostic tools and/or therapeutic agents.

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1R,2R,4S,5R)-3-methyleneneoisoverbanol and (1R,2R,3R,5R)-4-methyleneneoisopinocampheol, to allylphosphine oxides. Hydroxy groups were introduced stereoselectively through a hydroboration–oxidation reaction proceeding from the less hindered site providing a trans relationship between the hydroxy and the phosphine substituents.

Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions

A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible α-deprotonation by a Cu(II)-OtBu species followed by further oxidation of the resulting Cu enolate.

Synthesis of Cyclic Enones by Allyl-Palladium-Catalyzed α,β-Dehydrogenation

The use of allyl-palladium catalysis for the one-step α,β-dehydrogenation of ketones via their zinc enolates is reported. The optimized protocol utilizes commercially available Zn(TMP)2 as base and diethyl allyl phosphate as oxidant. Notably, this transformation operates under salt-free conditions and tolerates a diverse scope of cycloalkanones.

Allyl-Palladium-Catalyzed Ketone Dehydrogenation Enables Telescoping with Enone α,β-Vicinal Difunctionalization

The telescoping of allyl-palladium catalyzed ketone dehydrogenation with organocuprate conjugate addition chemistry allows for the introduction of aryl, heteroaryl, vinyl, acyl, methyl, and other functionalized alkyl groups chemoselectively to a wide variety of unactivated ketone compounds via their enone counterparts. The compatibility of the dehydrogenation conditions additionally allows for efficient trapping of the intermediate enolate with various electrophiles. The utility of this approach is demonstrated by comparison to several previously reported multistep sequences.

Oligomer-cannabinoid conjugates

The invention relates to (among other things) oligomer-cannabinoid conjugates and related compounds. A conjugate of the invention, when administered by any of a number of administration routes, exhibits advantages over previously administered un-conjugated cannabinoid compounds.

Catalytic epoxidation of cyclic alkenes with air over CoOx/zeolite heterogeneous catalysts

The supported CoOx/zeolites have been prepared and applied for the epoxidation of cyclic alkenes with air. The catalysts are characterized by powder X-ray diffraction (XRD), ultraviolet-visible spectroscopy (UV-vis) and scanning electron microscope (SEM). Among these CoOx/zeolite catalysts, 2.4% CoOx/Y exhibits the best catalytic activity for the epoxidation of cis-cyclooctene with 61.2 mol% conversion and 98.8 mol% selectivity of epoxide. Some factors such as the kind of zeolites, the oxidants, the solvents, the Co contents, the reaction temperature and time play important roles in controlling the epoxidation. The recyclable stability of the 2.4% CoOx/Y catalyst is confirmed.

Synthesis of cyclobakuchiols A, B, and C by using conformation-controlled stereoselective reactions

Cyclohexanone with the pMeOC6H4 and CH 2/C(Me) substituents at the C3 and C4-positions was prepared from (+)-β-pinene and converted to the allylic picolinate by a Masamune-Wittig reaction followed by reduction and esterification. Allylic substitution of this picolinate with Me2CuMgBr×MgBr2 in the presence of ZnI2 proceeded with γ regio- and stereoselectively to afford the quaternary carbon center on the cyclohexane ring with the CH2/CH and Me groups in axial and equatorial positions, respectively. This product was converted to cyclobakuchiol A by demethylation and to cyclobakuchiol C by epoxidation of the CH2/C(Me) group. For the synthesis of cyclobakuchiol B, the enantiomer of the above cyclohexanone derived from (-)-β-pinene was converted to the cyclohexane-carboxylate, and the derived enolate was subjected to the reaction with CH2/CHSOPh followed by sulfoxide elimination to afford the intermediate with the quaternary carbon center with MeOC(/O) and CH2/CH groups in axial and equatorial positions. The MeOC(/O) group was transformed to the Me group to complete the synthesis of cyclobakuchiol B. Control is key! Synthesis of cyclobakuchiols A and C was stereoselectively accomplished by conformation-controlled substitution of allylic picolinate with Me2CuMgBr×MgBr2/ZnI 2. On the other hand, cyclobakuchiol B was synthesized by stereoselective addition of the cyclohexanecarboxylate enolate to CH 2/CHSOPh (see scheme). Copyright

A concise methodology for the synthesis of (-)-Δ9-tetrahydrocannabinol and (-)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.