20053-58-1

Upstream product

• 4497-92-1 2-carene 
• 498-15-7 (+)-Δ³-carene 

Downstream Products

• 5957-75-5 delta-8-tetrahydrocannabinol 
• 1972-08-3 dronabinol 
• 13956-29-1 CBD 
• 22972-55-0 abnormal cannabidiol 
• 65293-09-6 β-phellandrene-8-ol 
• 61262-80-4 (+)-p-menthadiene-3-ol acetate 
• 61302-39-4 (3S,4S)-4-Isopropyl-3-methoxy-1-methyl-cyclohexene 
• 61302-38-3 (3R,4S)-4-Isopropyl-3-methoxy-1-methyl-cyclohexene 
• 25437-28-9 trans-p-menth-1-en-3-ol 
• 34350-53-3 cis-p-menth-1-en-3-ol 
• 20053-40-1 cis-Δ²-p-menthene-1,8-diol 
• 1196995-04-6 (1S,2R,3R,6R)-3,7,7-trimethyl-2-(phenylselanyl)bicyclo[4.1.0]heptan-3-ol 
• 160299-94-5 (-)-cheimonophyllon E 
• 52154-82-2 (1R,4R)-p-mentha-2,8-dien-1-ol 

Relevant academic research and scientific papers

Syntheses of the optically active terpene hydroxyphenylselenides

The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence of the substrate structures on the composition of the obtained products has been demonstrated.

Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-β-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with β-hydroxy- and β-methoxytosylates. The influence of a hydroxy group at the β-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)).

Enantioselective baeyer-villiger oxidation catalyzed by palladium(II) complexes with chiral P,N-ligands

(Chemical Equation Presented) Asymmetric Baeyer-Villiger reaction of symmetrical cyclobutanones 1a-j with urea-hydrogen peroxide (UHP) can be catalyzed by a complex of Pd(II) and the new terpene-derived P,N-ligand 7. The resulting lactones 2a-j were obtained in high yields and with good enantioselectivity (≤81% ee).

METHODS AND INTERMEDIATES FOR THE SYNTHESIS OF DELTA-9 TETRAHYDROCANNABINOL

Processes are disclosed for the synthesis of Delta-9 tetrahydrocannabinol which result in an improved Y-THC/Y-THC ratio, and intermediates are disclosed that may be used in the synthesis of Delta-9 tetrahydrocannabinol such that improved Y-THCIY-THC ratios are achieved. The intermediates may be cyclic compounds prepared from 2-Carene. There is also provided a scaleable process for the preparation of (+)-p-menth-2-ene-1, 8-diol,, another intermediate used in the synthesis of delta-9-tetrahydrocannibinol.

The enantioselective syntheses of bisabolane sesquiterpenes Lepistirone and Cheimonophyllon E

The synthetic approach to the bisabolane sesquiterpenes Lepistirone 1 and Cheimonophyllon E 2 involves the transformation of (+)-2-carene (5) into the p-menthane furans 8 and 11. Regio- and stereoselective alkylation, and standard reactions complete the e

Synthesis of new chiral 2,2′-bipyridine ligands and their application in Copper-catalyzed asymmetric allylic oxidation and cyclopropanation

A series of modular bipyridine-type ligands 1 and 3-9 has been synthesized via a de novo construction of the pyridine nucleus. The chiral moieties of these ligands originate from the isoprenoid chiral pool, namely, β-pinene (10 → 1), 3-carene (14 → 3 and 5), 2-carene (28 → 4), α-pinene (43 → 6-8), and dehydropregnenolone acetate (48 → 9), respectively. Copper(I) complexes, derived from these ligands and (TfO)2Cu (1 mol%) upon an in situ reduction with phenylhydrazine, exhibit good enantioselectivity (up to 82% ee) and unusually high reaction rate (typicaly 30 min at room temperature) in allylic oxidation of cyclic olefins (52 → 53). Copper-catalyzed cyclopropanation proceeded with ≤76% enantioselectivity and ～3:1 to 99:1 trans/cis-diastereoselectivity (54 → 55 + 56). The level of the asymmetric induction is discussed in terms of the ligand architecture that controls the stereochemical environment of the coordinated metal.

Substrate-induced diastereoselectivity in the dimethyldioxirane epoxidation of simple alkenes and dienes

Various alkenes and dienes, such as (R)- or (S)-limonene 2, 2-carene 6, 3-carene 8, (R)-α-pinene 10, (S)-α-pinene 12, and endo-dicyclopentadiene 14 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution). The selectivity observed in these epoxidations is explained by the assumption of hydrogen bonding between bridge protons and the dioxirane.

Modular pyridine-type P,N-ligands derived from monoterpenes: Application in asymmetric Heck addition

Novel (diphenylphosphinophenyl)pyridine ligands (+)-8, (+)-15, (-)-21, and (-)-26 were synthesized from (-)-β-pinene, (+)-3-carene, (+)-2-carene, and (-)-α-pinene, respectively, via Kro?hnke annulation as the key step, and shown to effect ≤88% ee in Heck addition (27→28). Ligands (+)-15 and (-)-21 are quasi-enantiomeric; ligands 8 and 26 can be prepared in both enantiomeric forms from (+)- and (-)-enantiomers of α- and β-pinene, respectively.

Acid-catalysed Terpenylations of Olivetol in the Synthesis of Cannabinoids

Examination of the toluene-p-sulphonic acid-catalysed reaction of (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide with olivetol shows that, inconsistently with the accepted mechanism, (3R,4R)-(-)-o- and -p-cannabidiols are produced as well as (3R,4R)-(-)-Δ1- and Δ6-tetrahydrocannabinols.Evidence is now presented that, as in Petrzilka's reaction employing chiral p-mentha-2,8-dien-1-ols, the reacting species is the delocalised (4R)-p-mentha-2,8-dien-1-yl cation (9).Similar terpenylation using (1S,3S,4R,6R)-(+)-trans-car-3-ene epoxide shows that besides the reported (-)-Δ6-THC, o- and p-cannabidiols, Δ1-THC and Δ4,8-iso-THC can also be produced.The nature of the products, the chirality, and the characteristics of the reaction implicate again the delocalised cation (9).Its formation via Kropp-type rearrangement is excluded and a pathway leading to (4R)-p-mentha-2,6,8-triene, which on protonation gives (9), is proposed.Protonated on C-8, the triene can be trapped and isolated as (4R)-p-mentha-2,6-dien-8-ol.The latter, made in (+/-)-form from citral, proved to be an excellent terpenylating agent for producing cannabinoids.Terpenylation of olivetol by the pinanes (1S,4S,5S)-(-)-cis-verbenol and (1R,5S,7R)-(+)-cis-chrysanthenol is compared.A major drawback of the latter is partial racemisation which occurs in the verbenone-chrysanthenone isomerisation during its photochemical preparation.Whilst Δ1-THC cannot be directly obtained from verbenol, its tertiary allylic cation permits a much higher yielding terpenylation than the secondary cation from chrysanthenol.