1-(1-hydroxynaphthalen-2-yl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 8.29 g (0.06 mole) of bicyclo[3,3,1]nonan-9-one and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene, and the solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of this chromanol compound was heated at 150° C. to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes, and the obtained brown viscous liquid was purified by the chromatography on silica gel to obtain 6.9 g of a chromene compound represented by the following formula: ##STR161## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 8.29 g (0.06 mole) of bicyclo[3,3,1]nonan-9-one and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene, and the solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of this chromanol compound was heated at 150° C. to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes, and the obtained brown viscous liquid was purified by the chromatography on silica gel to obtain 6.9 g of a chromene compound represented by the following formula: ##STR161## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 6.6 g (0.06 mole) of norcamphor and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene. The solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol, and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of the chromanol compound was heated at 150° C. to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained viscous liquid was purified by the chromatography on silica gel to obtain 6.3 g of a chromene compound of the following formula: ##STR70## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 6.6 g (0.06 mole) of norcamphor and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene. The solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol, and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of the chromanol compound was heated at 150° C. to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained viscous liquid was purified by the chromatography on silica gel to obtain 6.3 g of a chromene compound of the following formula: ##STR70## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), 1-hydroxy-2-acetonaphthone (250 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 2 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give the title compound (5 mg, yield 30%). The reaction solution was cooled to room temperature the mixture was extracted with ethyl acetate The ethyl acetate layer was then washed with water and saturated brine was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g of 1-hydroxy-2-acetylnaphthalene are dissolved in 60 ml of dioxane, and 30 ml of 30% sodium hydroxide solution are added. At a temperature of from 70° C. to 80° C., difluorochloromethane (Freon 22) is introduced until no further absorption is observed. The dioxane phase is then decanted, the NaOH phase is washed with dioxane, the dioxane phase is decanted, and the combined dioxane solutions are largely concentrated in vacuo using a rotary evaporator. Water is added to the residue, the mixture is extracted several times with diethyl ether, and the diethyl ether solution is dried over Na2SO4, filtered and concentrated by evaporation. The residue is recrystallised from diethyl ether/hexane. Yield: 4 g, m.p. 80°-81° C. The dioxane phase is then decanted the NaOH phase is washed with dioxane the dioxane phase is decanted the combined dioxane solutions are largely concentrated in vacuo a rotary evaporator Water is added to the residue the mixture is extracted several times with diethyl ether the diethyl ether solution is dried over Na2SO4 filtered concentrated by evaporation The residue is recrystallised from diethyl ether/hexane

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Chloro-6,7-dimethoxyquinoline (100 mg), 1-hydroxy-2-acetonaphthone (250 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 2 hr. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-chloroform to give the title compound (5 mg, yield 30%). The reaction solution was cooled to room temperature the mixture was extracted with ethyl acetate The ethyl acetate layer was then washed with water and saturated brine was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g of 1-hydroxy-2-acetylnaphthalene are dissolved in 60 ml of dioxane, and 30 ml of 30% sodium hydroxide solution are added. At a temperature of from 70° C. to 80° C., difluorochloromethane (Freon 22) is introduced until no further absorption is observed. The dioxane phase is then decanted, the NaOH phase is washed with dioxane, the dioxane phase is decanted, and the combined dioxane solutions are largely concentrated in vacuo using a rotary evaporator. Water is added to the residue, the mixture is extracted several times with diethyl ether, and the diethyl ether solution is dried over Na2SO4, filtered and concentrated by evaporation. The residue is recrystallised from diethyl ether/hexane. Yield: 4 g, m.p. 80°-81° C. The dioxane phase is then decanted the NaOH phase is washed with dioxane the dioxane phase is decanted the combined dioxane solutions are largely concentrated in vacuo a rotary evaporator Water is added to the residue the mixture is extracted several times with diethyl ether the diethyl ether solution is dried over Na2SO4 filtered concentrated by evaporation The residue is recrystallised from diethyl ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 6.6 g (0.06 mole) of norcamphor and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene. The solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol, and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of the chromanol compound was heated at 150° to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained viscous liquid was purified by the chromatography on silica gel to obtain 6.3 g of a chromene compound of the following formula: ##STR67## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 6.6 g (0.06 mole) of norcamphor and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene. The solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol, and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of the chromanol compound was heated at 150° to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained viscous liquid was purified by the chromatography on silica gel to obtain 6.3 g of a chromene compound of the following formula: ##STR67## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution was prepared by dissolving 10 g (0.054 mole) of 1-hydroxy-2-acetonaphthone, 6.6 g (0.06 mole) of norcamphor and 8 g (0.113 mole) of pyrrolidine in 300 cc of toluene. The solution was boiled for 10 hours and water was separated. After termination of the reaction, toluene was removed under reduced pressure, and the remaining chromanone compound was crystallized with acetone. Then, the chromanone compound was dissolved in 200 cc of methanol, and sodium boron hydride was gradually added to the solution to form a chromanol compound. Then, 7.47 g of the chromanol compound was heated at 150° to 160° C. together with 4.5 g of anhydrous copper sulfate in a carbon dioxide current for 10 minutes and the obtained viscous liquid was purified by the chromatography on silica gel to obtain 6.3 g of a chromene compound of the following formula: ##STR67## A solution was prepared water was separated After termination of the reaction, toluene was removed under reduced pressure the remaining chromanone compound was crystallized with acetone Then, the chromanone compound was dissolved in 200 cc of methanol sodium boron hydride was gradually added to the solution

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1-hydroxy-2-acetonaphthone 1 (15 g, 81 mmol) and 3,4,5-trimethoxy-benzaldehyde 2 (17.66 g, 88 mmol) in 600 mL ethanol was treated with piperidine (40 mL) and pyridine (45 mL) and the dark solution was refluxed for 18 h. The reaction mixture was evaporated to dryness and the dark residue was dissolved in methylene chloride (600 mL). The solution was washed with 2×300 mL of water and 2×300 mL brine and dried with anhydrous MgSO4 after which it was filtered and evaporated to afford 60 g of crude material. This was purified via flash chromatography, eluting with methylene chloride (1 L), followed by the solvent mixture CH2Cl2: EtOAc (95:5) to obtain fractions containing pure product. These were evaporated to afford 11.4 g (39% yield) of pure SR 13177 as a yellow solid. TLC: Hexanes/EtOAc (7:3): Rf=0.26; 1H NMR (300 MHz, CDCl3): δ 3.00 (dd, J=16.69, 3.15, 1H, 3-H), 3.22 (dd, J=16.94, 13.28, 1H, 3-H), 3.92 and 3.94 (2s, 9H, OCH3), 5.66 (dd, J=13.31, 3.17, 1H, 2-H), 6.81 (s, 2H, 2′,6′-Ar—H), 7.46-7.95 (m, 5H, Ar—H), 8.36 (d, 1H, Ar—H); 13C (75 MHz, CDCl3): δ 44.27 (C-3), 56.35 (OCH3), 60.89 (OCH3), 80.62 (C-2), 103.49, 115.61, 121.47, 123.61, 124.91, 126.34, 127.94, 129.71, 134.4, 137.67, 153.68, 159.71, 191.42. Anal. calcd. for C22H20O5; C, 72.51; H, 5.53; Found: C, 72.35; H, 5.64. the dark solution was refluxed for 18 h The reaction mixture was evaporated to dryness the dark residue was dissolved in methylene chloride (600 mL) The solution was washed with 2×300 mL of water and 2×300 mL brine dried with anhydrous MgSO4 after which it was filtered evaporated to afford 60 g of crude material This was purified via flash chromatography eluting with methylene chloride (1 L) to obtain fractions containing pure product These were evaporated