41303-46-2Relevant articles and documents
Asymmetric 1,4-addition of organoboron reagents to quinone monoketals catalyzed by a chiral diene/rhodium complex: A new synthetic route to enantioenriched 2-aryltetralones
Tokunaga, Norihito,Hayashi, Tamio
, p. 513 - 516 (2008/02/08)
A novel synthetic approach to 2-aryltetra-lones with high ee has been developed through asymmetric 1,4-addition of arylboronic acids to naphthoquinone monoketals catalyzed by a rhodium complex with the (R,R)-Ph-bod* ligand. The asymmetric addition proceed
Studies on the chemical constituents of rutaceous plants. L. Development of a versatile method for the synthesis of antitumor-active benzo[c]phenanthridine alkaloids. (2). Preparation of 2-aryl-1-tetralone derivatives
Ishii,Kawanabe,Harada,et al.
, p. 3039 - 3055 (2007/10/02)
The synthetic pathway from 2,4-bisaryl-4-oxobutyramide (3) to 2-aryl-1-tetralone (4), which is the key intermediate in the Robinson synthesis of antitumor-active benzo[c]phenanthridine alkaloids was improved. Treatment of the model keto-amide (3a) under the reported basic conditions gave γ-keto-α,β-unsaturated acid (9) and degradation products. Reduction of the 2,4-bisaryl-4-oxobutyramide (3) with sodium borohydride gave 2,4-bisaryl-4-hydroxybutyramide (16) which could easily be hydrogenolyzed to give 2,4-bisarylbutyramide (15). However, this transformation also tended to give a γ-lactam derivative (17), unfortunately. We succeeded in the direct hydrogenolysis of the 2,4-bisaryl-4-oxobutyramide (3) to the 2,4-bisarylbutyramide (15), which could be hydrolyzed to the corresponding acid (5) without difficulty. The direct hydrolysis of the 2,4-bisaryl-4-oxobutyronitrile (2) to the 2,4-bisaryl-4-oxobutyric acid (6) as reported by Cheng et al. was also examined. Ten 2-aryl-1-tetralones (4) required as starting materials for syntheses of various benzo[c]phenanthridine alkaloids were prepared.