79767-50-3

Upstream product

• 69575-87-7 (-)-(1R,2S,5R,6S)-bicyclo<3.3.1>nonane-2,6-diol 
• 16473-11-3 bicyclo[3.3.1]nonane-2,6-dione 
• 1092543-24-2 6-hydroxybicyclo[3.3.1]nonan-2-one 
• 16473-11-3 bicyclo[3.3.1]nonane-2,6-dione 

Relevant academic research and scientific papers

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.

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.

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.

Synthesis and chiroptical properties of enantiopure tricyclo[4.3.0.03,8]nonane-4,5-dione (twistbrendanedione)

The synthesis of chiral tricyclo[4.3.0.03,8]nonane-4,5-dione was accomplished starting from enantiomerically pure (+)-(1S,5S)-bicyclo[3.3.1]nonane-2,6-dione 1. Ring contraction of the latter with thallium(III) nitrate proceeded with high stereo

Synthesis and chiroptical properties of methanocycloocta[6]indoles

The synthesis of chiral methanocyclocta[6]indoles, the fused structures obtained from enantiomeric bicyclo[3.3.1]nonanones via Fisher indolization reaction, is reported. The starting optically active bicyclo[3.3.1]nonane-2,6-dione (1) was obtained by a chiral HPLC enantiomer separation on a swollen microcrystalline triacetylcellulose column and by the enzymatic resolution of the racemic dione. The circular dichroism (CD) spectra of the chiral structures 4, 5, and 7 were recorded, and the absolute configuration for the indole compounds was assigned. The theoretical calculations of the CD spectrum of diindole 4 reproduce the aBb couplet at 229 nm but predict wrong signs for the 1La and 1Lb bands using standard polarization directions. The CD spectrum of indole ketone 5 is reproduced correctly.

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.