86835-18-9

Upstream product

• 122172-25-2 (S)-2-[1,3]Dithiolan-2-yl-2-(4-methoxy-phenyl)-4-(2-methyl-[1,3]dithiolan-2-yl)-butyric acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 141750-58-5 (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3S,5R,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoate 

Downstream Products

• 86835-31-6 2-Diazo-3-oxo-6-phenyl-hexanoic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 122172-23-0 (2R,3R)-1,7,7-trimethyl-2-(1-naphthyl)bicyclo<2.2.1>hept-3-yl 2-(4-methoxyphenyl)-3-oxopropanoate 
• 110971-10-3 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-3-phenylpropanoate 
• 110971-08-9 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-cyclohexyl-3-oxopropanoate 
• 110971-12-5 4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl 3-oxo-4-phenylbutanoate 
• 86835-36-1 (R)-2-Oxo-5-phenyl-cyclopentanecarboxylic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 86835-36-1 (S)-2-Oxo-5-phenyl-cyclopentanecarboxylic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 210585-36-7 N-(4-Methoxy-phenyl)-N-[2-(3-nitro-phenyl)-ethyl]-malonamic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 210585-34-5 N-(4-Methoxy-phenyl)-N-[2-(2-methoxy-phenyl)-ethyl]-malonamic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 210585-35-6 N-(4-Methoxy-phenyl)-N-[2-(3-methoxy-phenyl)-ethyl]-malonamic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 
• 210585-32-3 N-(4-Methoxy-phenyl)-N-phenethyl-malonamic acid (1S,2R,3R,4S)-4,7,7-trimethyl-3-naphthalen-1-yl-bicyclo[2.2.1]hept-2-yl ester 

Relevant academic research and scientific papers

Stereoselective reduction of β,δ-diketo esters. A novel strategy for the synthesis of artificial HMG-CoA reductase inhibitors

Condensation of N-methoxy-N-methyl amides with the dianions of acetoacetates gives in good yields β,δ-diketo esters, which are reduced with Et2BOMe-NaBH4 in tetrahydrofuran-methanol highly selectively to give syn-β,δ-dihydroxy esters in one step. Similarly, the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer respectively are reduced to give syn-β,δ-dihydroxy esters of moderate enantiomeric excess. Higher diastereo- and enantioselectivity were achieved by reduction of the β,δ-diketo esters of the Taber's chiral alcohol or its enantiomer successively with diisobutylalane and with Et2BOMe-NaBH4. The resulting syn-diol esters were hydrolyzed and lactonized to give various types of β-hydroxy-δ-lactones commonly found in artificial HMG-CoA reductase inhibitors.

Enantioselective Robinson Annulation: Synthesis of (+)-O-Methyljoubertiamine

The α-formyl ester derived from 2-(1-naphthyl)-3-borneol, as the potassium salt in moist dimethoxymethane, adds to methyl vinyl ketone to give two adducts in a ratio of 95:5.The relative configuration of the major diastereomer has been confirmed by X-ray crystallography.This diastereomer is readily carried on to (+)-O-methyljoubertiamine.The addition of such naphthylbornyl esters to Michael acceptors should constitute a general laboratory-scale procedure for the enantioselective construction of enantiomerically pure quaternary stereogenic centers.