36415-87-9

Upstream product

• 16473-11-3 bicyclo[3.3.1]nonane-2,6-dione 
• 69575-88-8 (+)-(1S,2R,5S,6R)-bicyclo<3.3.1>nonane-2,6-diol 
• 16473-11-3 bicyclo[3.3.1]nonane-2,6-dione 
• 69575-86-6 C₂₉H₄₀O₈ 

Downstream Products

• 899789-29-8 (1S,5S)-bicyclo[3.3.1]nonane-2,6-dione bis[(1-benzyl-6-methyl-2-oxo-1,2-dihydro-4-pyridinyl)hydrazone] 
• 1433725-25-7 (S,S)-6-methylbicyclo[3.3.1]nona-6-en-2-one 4-methylbenzenesulfonhydrazone 

Relevant academic research and scientific papers

Enantiospecific synthesis and chiroptical properties of bicyclic enones

The enantiospecific synthesis of several bicyclic enones starting from enantiomerically pure (+)-(1S,5S)-bicyclo[3.3.1]-nonane-2,6-dione (1) was accomplished. The target enones 7-9 were obtained in high yield and purity by using a catalytic amount of benzeneselenic anhydride. (+)-(1S,5R)-bicyclo[3.3.1] nonane-2,3,6-trione was obtained from diketone 1 by α-hydroxylation involving the use of iodine under basic conditions. The reaction included a ring closure/reopening sequence via oxatricyclo[4.3.1.03,8]decane-10-one. It was shown that the latter triketone exists in enone/enol form. Chiroptical properties of the enantiomerically pure compounds were studied, and the sign of the Cotton effect was related to the absolute configuration of the enones. The positive Cotton effect in the bisignate CD curve is accounted for by the nonplanarity of the chromophore in enones (1S,5R)-4 and (1S,5S)-8. The circular dichroism spectra provided evidence for interchromophoric interaction in dichromophoric bis(enone) 9. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Enzymatic enantioseparation of bicyclo[3.3.1]nonane-2,6-diones

Preparative enantioseparation of the (+)-and (-)-enantiomers of bicyclo[3.3.1]nonane-2,6-dione was performed by means of a horse liver alcohol dehydrogenase catalyzed reduction, coupled with the regeneration of the coenzyme NAD by dithionite or ethanol.

Synthesis of enantiomerically pure (+)-(1S,2R,5S,6R)-endo,endo-2,6-diaminobicyclo[3.3.1]nonane

Enantiospecific synthesis of enantiomerically pure (+)-(1S,2R, 5S,6R)-endo,endo-2,6-diaminobicyclo[3.3.1]nonane was accomplished via a reaction sequence including stereospecific synthesis of the corresponding dinitro compound and the subsequent reduction of the latter with LiAlH4. The title diamine wasalso obtained in a direct reduction of the corresponding dioxime with sodium in ethanol with high stereoselectivity.

Genetically engineered Saccharomyces cerevisiae for kinetic resolution of racemic bicyclo[3.3.1]nonane-2,6-dione

Whole cells of the genetically engineered Saccharomyces cerevisiae strain TMB4100 (1% PGI, YMR226c) were used as the biocatalyst for the kinetic resolution of racemic bicyclo[3.3.1]nonane-2,6-dione rac-1. The yeast's phosphoglucose isomerase activity was decreased, and the short-chain dehydrogenase/reductase encoded by YMR226c was overexpressed. This reduced the demand for the glucose to regenerate NADPH, while at the same time the reaction rate and selectivity towards (-)-1 became higher. The demand for yeast biomass also decreased, facilitating down-stream processing, which is of considerable importance on a large scale. With 15 g dry weight/L of the genetically engineered yeast TMB4100 (1% PGI, YMR226c), 40 g/L rac-1 was kinetically resolved within 24 h producing pure (+)-1 with an enantiomeric excess (ee) of 100% after 75% conversion. This corresponds to a biochemical selectivity constant of E = 10.3 ± 2.2. Thus, compared with conventional methods which use commercial baker's yeast as a biocatalyst, the reaction system was significantly improved, and would be superior in a large-scale process.

EIN RASCHER ZUGANG ZU OPTISCH AKTIVEN ADAMANTAN-DERIVATEN

The stereospecific reduction using baker's yeast is an easy and efficient method for the resolution of bicyclononane-2,6-dione in a preparative scale from which optically active adamantane compounds are readily available.

Open and rearranged norbornane derived polycyclic cage molecules as potential neuroprotective agents through attenuation of MPP+- and calcium overload-induced excitotoxicity in neuroblastoma SH-SY5Y cells

The neuroprotective effects of closed polycyclic cage molecules such as NGP1-01, memantine and amantadine have been extensively explored. These effects are mostly linked to the antagonism of the N-methyl-D-aspartate (NMDA) receptor- and the blockage of vo

Asymmetric cross-dimerization between methyl methacrylate and substituted alkene by Ru(0)-bicyclononadiene complex

New Ru(0)-naphthalene complexes containing a bicyclononadiene ligand catalyze the linear cross-dimerization between methyl methacrylate and substituted alkenes by an oxidative coupling mechanism. The chiral (S,S)-2-methylbicyclo[3.3.1]nona-2,6-diene complex (S,S)-1b catalyzes asymmetric linear cross-dimerization between methyl methacrylate and 2,5-dihydrofuran to give the cross-dimer in 74% yield in 80% ee.

Stereoselective bioreduction for the resolution of racemic mixtures of bicyclo[3.3.1]nonane-2,6-dione using vegetables

Screening of various vegetables as biocatalysts for the stereoselective bioreduction and resolution of racemic bicyclo[3.3.1]nonane-2,6-dione was performed. Vegetables of the family Apiaceae, i.e. the roots of parsnip (Pastinaca sativa), celery (Apium gra

Baker's yeast for sweet dough enables large-scale synthesis of enantiomerically pure bicyclo[3.3.1]nonane-2,6-dione

An improved synthetic procedure of racemic bicyclo[3.3.1]nonane-2,6-dione has been developed. Employing Baker's yeast for sweet dough made it possible to kinetically resolve the racemic compound and to isolate enantiomerically pure (+)-bicyclo[3.3.1]nonane- 2,6-dione on a large scale. Furthermore, the developed procedure made it possible to produce (-)-bicyclo[3.3.1]nonane-2,6-dione with an enantiomeric excess of 75%. Georg Thieme Verlag Stuttgart.

Synthesis and rhodium complexation of enantiomerically enriched bicyclo[3.3.1]nona-2,6-diene

Enantiomerically enriched (S,S)-bicyclo[3.3.1]nona-2,6-diene has been synthesised from the readily available diketone (S,S)-bicyclo[3.3.1]nonane-2,6-dione. The stereochemical purity is maintained on complexation to rhodium. There is a very strong preference for the formation of the homochiral over the heterochiral (alkene)2Rh+ OTf- complex; the self-recognition involved can be rationalised by analysis of DFT calculations.