368875-09-6

Upstream product

• 607680-03-5 (3aS,7aS)-3a-methyloctahydroinden-1-one 
• 53068-89-6 (R)-(+)-2-(2'-carbomethoxyethyl)-2-methylcyclohexanone 
• 607680-04-6 (3aS,7aS)-7a-hydroxy-3a-methyloctahydroinden-1-one 
• 583-60-8 2-Methylcyclohexanone 
• 55046-90-7 1-(3-Hydroxy-prop-1-ynyl)-2-methyl-cyclohexanol 
• 368875-07-4 acetic acid 3α-methyl-3,3',4,5,6,7-hexahydro-2H-inden-1-yl ester 
• 368875-06-3 3α-methyloctahydroinden-1-one 
• 53068-89-6 (S)-3-(1-methyl-2-oxocyclohexyl)-propionic acid methyl ester 
• 368875-08-5 7-hydroxy-3α-methyl-octahydroinden-1-one 

Relevant academic research and scientific papers

On the bioactive conformation of the rhodopsin chromophore: Absolute sense of twist around the 6-s-cis bond

Incubation of opsin with synthetic 6-s-locked retinoids 2a and 2b only led to pigment formation from the alpha-locked 2a, the CD spectrum of which was similar to that of native rhodopsin (Rh). This establishes that the 6-s-bond of the chromophore in rhodo

Facile cleavage of vicinal tertiary diols by pyridinium dichromate

Vicinal tertiary diols with diaxial hydroxyl groups are cleaved selectively by PDC (pyridinium dichromate) under mild conditions to give the corresponding diketones in high yields.

Regio- and Stereoselective Cyclopentannulation with Ketones and Propargyl Alcohol Derivatives. Synthesis of dl-Nootkatone and dl-Muscopyridine

A highly regio- and stereoselective five-membered ring annulation involving the acid-treatment of propargyl alcohol dianion adducts of ketones is described.The propargyl alcohol adduct of 2-octanone was converted into 2-methyl-3-pentyl-2-cyclopentenone by treatment with sulfuric acid-methanol (1:1) at 0 deg C.As the major product, 1-methylbicyclodec-6-en-8-one was produced from 2-methylcycloheptanone.Remarkable regioselective cyclopentannulation was observed in 2-methylcyclohexanone and 2,3-dimethylcyclohexanone wherein 1-methyl- and trans-1,2-dimethyl-substituted bicyclonon-5-en-7-one (BNO) are produced, respectively.With 3-butyn-2-ol, 2-methylcyclohexanone was converted into the cis-1,9-dimethyl-substituted BNO. 4-Isopropyl-2-methylcyclohexanone was transformed into an 83-85:17-15 mixture of c-3-isopropyl-r-1,c-9-dimethyl-BNO and its 3-epimer.These results are explained in terms of the conrotatory ring-closure of thermodynamically most favorable hydroxypentadienyl cation intermediates. 3-Methoxycarbonyl-cis-1,9-dimethyl-BNO produced from 4-methoxycarbonyl-2-methylcyclohexanone and 3-butyn-2-ol was successfully transformed into dl-nootkatone by converting the methoxycarbonyl group into isopropenyl of correct stereochemistry followed by ring enlargement.Cyclopentannulation using propargyl alcohol dianion adducts of 2-cycloalkenones is discussed.Annulation takes place regioselectively to give conjugated dienones, e.g., (E)-bicyclopentadeca-1(12),2-dien-13-one from 2-cyclododecenone.This product is led to dl-muscopyridine by conjugate 1,6-addition of methyl group followed by ring expansion and finally by aromatization with hydroxylamine hydrochloride.