34413-89-3

Upstream product

• 2494-10-2 1-piperidinomethanol 
• 38651-65-9 (1R,5S)-(+)-nopinone 
• 50-00-0 formaldehyd 

Downstream Products

• 388066-93-1 (6R,8R)-7,7-dimethyl-2-[1-(phenylmethoxy)ethyl]-5,6,7,8-tetrahydro-6,8-methanoquinoline 
• 409319-28-4 (6R,8R)-(+)-5,6,7,8-tetrahydro-7,7-dimethyl-2-(2-methoxyphenyl)-6,8-methanoquinoline 
• 157059-20-6 methylene bis(3,3'-(6,6-dimethylbicyclo(3.1.1)heptan-2-one)) 
• 1335146-09-2 4-{4-[(1R,5R)-2-(4-Chloro-phenyl)-2-hydroxy-6,6-dimethyl-bicyclo[3.1.1]hept-3-ylmethyl]-piperazin-1-yl}-benzoic acid ethyl ester 
• 1335146-10-5 4-{4-[(1R,5R)-2-(4-Chloro-phenyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-3-ylmethyl]-piperazin-1-yl}-benzoic acid ethyl ester 
• 457926-47-5 (4RS,5R,7R)-4-benzyloxy-5,7-methano-6,6-dimethyl-1,2,3,4,5,6,7,8-octahydroacridine 
• 349472-86-2 (1R,9R)-4-(2-Fluoro-phenyl)-10,10-dimethyl-3-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 21725-96-2 6,6-dimethyl-3'-phenyl-4'H-spiro[bicyclo[3.1.1.]heptane-3,5'-isoxazol]-2-one 

Relevant academic research and scientific papers

Platinum(II) compounds with enantiomerically pure bis(pinene)-fused bipyridine ligands - Diimine-dichloro complexes and their substitution reactions

The synthesis of chiral square-planar PtII complexes using symmetrical and unsymmetrical bis(pinene)-fused 2,2′-bipyridine is described. The neutral diimine dichloro complexes show a strong deviation of the coordination sphere from planarity if the pinene groups are attached at the 5-and 6-positions of the pyridine rings. However, this distortion does not occur in parallel with the chiral configuration at the diimine ligands. The substitution of the two cis-chloro ligands with diamines to form five-membered chelate rings shows little diastereoselectivity when racemic mixtures of chiral diamines are used. Also, ligands that are prochiral at the ligating centers show little selectivity upon coordination.

Synthesis and oxidative transformations of new chiral pinane-type γ-ketothiols: Stereochemical features of reactions

Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)2 catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed.

APOPTOSIS-INDUCING AGENTS FOR THE TREATMENT OF CANCER AND IMMUNE AND AUTOIMMUNE DISEASES

Disclosed are compounds which inhibit the activity of anti-apoptotic Bcl-2 proteins, compositions containing the compounds and methods of treating diseases during which is expressed anti-apoptotic Bcl-2 protein.

Synthesis of chiral C2-symmetric 1,10-phenanthrolines from naturally occurring monoterpenes

A convenient procedure for the preparation of chiral C2-symmetric 1,10-phenanthrolines bearing a chiral framework in the form of a cycloalkeno-condensed substituent in the 2,3- and 8,9-positions of the heterocycle is reported. Starting from the 2-benzyloxycyclohexanone, four 1,10-phenanthrolines derived from (-)-β-pinene, (+)-α-pinene, (-)-isopinocampheol, and (+)-camphor were prepared according to a method based on a double Michael-azaannulation-aromatization sequence.

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.

Synthesis of chiral thienylpyridines from naturally occurring monoterpenes: Useful ligands for cyclometallated complexes

On treatment with ammonium acetate, α,β-unsaturated ketones or aldehydes can easily undergo condensation with acetylpyridinium salts (Krohnke reaction). Four 'thienylpyridine' ligands, derived from (-)-β-pinene, (+)-camphor, (+)-3-carene and (+)-2-carene, were prepared according to this method. The multistep syntheses to get (1R,5R)-3-methylenenopinone (5), (+)-3-methylenecamphor (10), (-)-3-caren-10-al (15) and (1S,6R)-7,7-dimethyl-3-methylenebicyclo[4.1.0]heptan-2-one (18) are also described.