1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethanol

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

Procedure: A solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-ethanol (184 mg; 0.75 mmol), triphenylphosphine (268 mg; 1.0 mmol), diethyl azodicarboxylate (0.161 ml; 1.0 mmol) and (2S)-2-((2-benzoylphenyl)amino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (190 mg; 0.5 mmol) in THF (10 ml) was stirred at 0° C. for 1.5 hours and for 16 hours at room temperature. The reaction mixture was evaporated and the residue was purified on column chromatography using methylene chloride as eluent. Yield 118 mg. The reaction mixture was evaporated the residue was purified on column chromatography

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

Procedure: A solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol (246 mg; 1.0 mmol), triphenylphosphine (262 mg; 1.0 mmol), diethyl azodicarboxylate (0.153 ml; 1.0 mmol) and 4-hydroxybenzaldehyde (183 mg; 1.5 mmol) in THF (20 ml) was stirred at 0° C. for 1.5 hours and for 16 hours at room temperature. Water was added (20 ml) and the mixture was extracted with methylene chloride (3×25 ml). The combined organic phases were dried and evaporated. The residue was purified on column chromatography using ethyl acetate: hexane (1:3) as eluent. Yield 180 mg. the mixture was extracted with methylene chloride (3×25 ml) The combined organic phases were dried evaporated The residue was purified on column chromatography

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

Procedure: To a solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (500 mg; 2.0 mmol) in dry THF (5 ml) was added slowly LiAlH4 (80 mg; 2.0 mmol) at 0° C. The reaction mixture was stirred for 3 hours, and then water (20 ml) was added. Ether (50 ml) was added and the mixture was filtered through filter aid. The organic phase was separated and the water phase was extracted with ether. The combined organic phases were dried and evaporated to give the title compound in 504 mg (100%) yield. the mixture was filtered through filter aid The organic phase was separated the water phase was extracted with ether The combined organic phases were dried evaporated

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

Procedure: To a solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (500 mg; 2.0 mmol) in dry THF (5 ml) was added slowly LiAlH4 (80 mg; 2.0 mmol) at 0° C. The reaction mixture was stirred for 3 hours, and then water (20 ml) was added. Ether (50 ml) was added and the mixture was filtered through filter aid. The organic phase was separated and the water phase was extracted with ether. The combined organic phases were dried and evaporated to give the title compound in 504 mg (100%) yield. the mixture was filtered through filter aid The organic phase was separated the water phase was extracted with ether The combined organic phases were dried evaporated

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.17 g (17.1 mmol) of methyl (5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2yl) ketone (Compound 16) in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid. at 0° C. Solvent was removed in-vacuo extracted three times with ether The ether extracts were washed with water, brine dried (MgSO4) The solvent was removed in-vacuo resulting residue purified to give a single isomer

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.17 g (17.1 mmol) of methyl [3,5,5,8,8-pentamethyl(5,6,7,8-tetrahydronaphthalen-2-yl] ketone (Compound 10) in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting :solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid. at 0° C. Solvent was removed in-vacuo extracted three times with ether The ether extracts were washed with water, brine dried (MgSO4) The solvent was removed in-vacuo resulting residue purified to give a single isomer

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.17 g (17.1 mmol) of methyl [3,5,5,8,8-pentamethyl(5,6,7,8-tetrahydronaphthalen-2-yl] ketone (Compound 10) in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid. at 0° C. Solvent was removed in-vacuo extracted three times with ether The ether extracts were washed with water, brine dried (MgSO4) The solvent was removed in-vacuo resulting residue purified to give a single isomer

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.17 g (17.1 mmol) of methyl[3,5,5,8,8-pentamethyl(5,6,7,8-tetrahydronaphthalen-2-yl]ketone in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid. at 0° C. Solvent was removed in-vacuo extracted three times with ether The ether extracts were washed with water, brine dried (MgSO4) The solvent was removed in-vacuo resulting residue purified to give a single isomer

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4.17 g (17.1 mmol) of methyl[3,5,5,8,8-pentamethyl(5,6,7,8-tetrahydronaphthalen-2-yl] ketone in methanol at 0° C. was portionwise added 0.77 g (20.4 mmol) of sodium borohydride and the resulting suspension stirred at 0° C. for 4 hours. Solvent was removed in-vacuo and the resulting solid taken-up in water, acidified using 1N HCl, and extracted three times with ether. The ether extracts were washed with water, brine and dried (MgSO4). The solvent was removed in-vacuo and resulting residue purified using flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give a single isomer: the title compound as a white solid. at 0° C. Solvent was removed in-vacuo extracted three times with ether The ether extracts were washed with water, brine dried (MgSO4) The solvent was removed in-vacuo resulting residue purified to give a single isomer

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

Procedure: A solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-ethanol (184 mg; 0.75 mmol), triphenylphosphine (268 mg; 1.0 mmol), diethyl azodicarboxylate (0.161 ml; 1.0 mmol) and (2S)-2-((2-benzoylphenyl)amino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (190 mg; 0.5 mmol) in THF (10 ml) was stirred at 0° C. for 1.5 hours and for 16 hours at room temperature. The reaction mixture was evaporated and the residue was purified on column chromatography using methylene chloride as eluent. Yield 118 mg. The reaction mixture was evaporated the residue was purified on column chromatography

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

Procedure: A solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol (246 mg; 1.0 mmol), triphenylphosphine (262 mg; 1.0 mmol), diethyl azodicarboxylate (0.153 ml; 1.0 mmol) and 4-hydroxybenzaldehyde (183 mg; 1.5 mmol) in THF (20 ml) was stirred at 0° C. for 1.5 hours and for 16 hours at room temperature. Water was added (20 ml) and the mixture was extracted with methylene chloride (3×25 ml). The combined organic phases were dried and evaporated. The residue was purified on column chromatography using ethyl acetate: hexane (1:3) as eluent. Yield 180 mg. the mixture was extracted with methylene chloride (3×25 ml) The combined organic phases were dried evaporated The residue was purified on column chromatography

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

Procedure: To a solution of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (500 mg; 2.0 mmol) in dry THF (5 ml) was added slowly LiAlH4 (80 mg; 2.0 mmol) at 0° C. The reaction mixture was stirred for 3 hours, and then water (20 ml) was added. Ether (50 ml) was added and the mixture was filtered through filter aid. The organic phase was separated and the water phase was extracted with ether. The combined organic phases were dried and evaporated to give the title compound in 504 mg (100%) yield. the mixture was filtered through filter aid The organic phase was separated the water phase was extracted with ether The combined organic phases were dried evaporated