tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ol

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0.595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° C. A round-bottom flask, equipped with a distillation apparatus Gas bubbles form and water and acetic acid are distilled through the condenser the mixture is cooled to room temperature dissolved in ethyl acetate The organic solution is washed with brine dried (magnesium sulfate) The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1

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

Procedure: A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0.595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° C. A round-bottom flask, equipped with a distillation apparatus Gas bubbles form and water and acetic acid are distilled through the condenser the mixture is cooled to room temperature dissolved in ethyl acetate The organic solution is washed with brine dried (magnesium sulfate) The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1

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

Procedure: Thus, as outlined in Scheme III, dibenzosuberol (XVI) is heated with malonic acid to about 160° C. to afford 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (XV). A solution of the acid (XV) in a solvent such as, for example, ethylene glycol dimethyl ether and the like in the presence of a base such as, for example, N,N-diisopropylethylamine and the like is reacted with pivaloyl chloride to afford the mixed anhydride (XIV) in situ.

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

Procedure: Thus, as outlined in Scheme III, dibenzosuberol (XVI) is heated with malonic acid to about 160° C. to afford 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (XV). A solution of the acid (XV) in a solvent such as, for example, ethylene glycol dimethyl ether and the like in the presence of a base such as, for example, N,N-diisopropylethylamine and the like is reacted with pivaloyl chloride to afford the mixed anhydride (XIV) in situ.

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

Procedure: A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0.595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° C. A round-bottom flask, equipped with a distillation apparatus Gas bubbles form and water and acetic acid are distilled through the condenser the mixture is cooled to room temperature dissolved in ethyl acetate The organic solution is washed with brine dried (magnesium sulfate) The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1

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

Procedure: Thus, as outlined in Scheme III, dibenzosuberol (XVI) is heated with malonic acid to about 160° C. to afford 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (XV). A solution of the acid (XV) in a solvent such as, for example, ethylene glycol dimethyl ether and the like in the presence of a base such as, for example, N,N-diisopropylethylamine and the like is reacted with pivaloyl chloride to afford the mixed anhydride (XIV) in situ.

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0.595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off-white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° C. A round-bottom flask, equipped with a distillation apparatus Gas bubbles form and water and acetic acid are distilled through the condenser the mixture is cooled to room temperature dissolved in ethyl acetate The organic solution is washed with brine dried (magnesium sulfate) The solvent is removed in vacuo to give an off-white solid, which is recrystallized from hexane-ethyl acetate/1:1

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

Procedure: A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0.595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off-white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° C. A round-bottom flask, equipped with a distillation apparatus Gas bubbles form and water and acetic acid are distilled through the condenser the mixture is cooled to room temperature dissolved in ethyl acetate The organic solution is washed with brine dried (magnesium sulfate) The solvent is removed in vacuo to give an off-white solid, which is recrystallized from hexane-ethyl acetate/1:1

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

Procedure: Thus, as outlined in Scheme III, dibenzosuberol (XVI) is heated with malonic acid to about 160° C. to afford 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (XV). A solution of the acid (XV) in a solvent such as, for example, ethylene glycol dimethyl ether and the like in the presence of a base such as, for example, N,N-diisopropylethylamine and the like is reacted with pivaloyl chloride to afford the mixed anhydride (XIV) in situ.

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

Procedure: Thus, as outlined in Scheme III, dibenzosuberol (XVI) is heated with malonic acid to about 160° C. to afford 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-acetic acid (XV). A solution of the acid (XV) in a solvent such as, for example, ethylene glycol dimethyl ether and the like in the presence of a base such as, for example, N,N-diisopropylethylamine and the like is reacted with pivaloyl chloride to afford the mixed anhydride (XIV) in situ.