dibutyl (2S,3S)-2,3-dihydroxybutanedioate

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

Procedure: 0.594 ml of titanium tetraisopropoxide was dissolved in 10 ml of dry methylene chloride. Thereupon, 524 mg of dibutyl D-tartrate were added dropwise at -20° C. and the mixture was left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol were then added and subsequently a further 180 mg of tert.butyl hydroperoxide (80%) were added dropwise (as a solution in 0.5 ml of methylene chloride). The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days, then treated with 5 ml of 1N sodium hydroxide solution, left to warm to room temperature and stirred for 1 hour. The phases were then separated, the aqueous phase was washed twice with methylene chloride, the organic phases were dried over sodium sulphate and concentrated. The colourless oil obtained was dissolved in 20 ml of ethyl ether and stirred with 5 ml of 1N sodium hydroxide solution for 1 hour. The phases were again separated, the aqueous phase was washed twice with ethyl ether, the organic phases were dried over sodium sulphate and concentrated. There were obtained 188 mg (98%) of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol. the mixture was left The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days left The phases were then separated the aqueous phase was washed twice with methylene chloride the organic phases were dried over sodium sulphate concentrated The colourless oil obtained The phases were again separated the aqueous phase was washed twice with ethyl ether the organic phases were dried over sodium sulphate concentrated

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

Procedure: 0.594 ml of titanium tetraisopropoxide was dissolved in 10 ml of dry methylene chloride. Thereupon, 524 mg of dibutyl D-tartrate were added dropwise at -20° C. and the mixture was left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol were then added and subsequently a further 180 mg of tert.butyl hydroperoxide (80%) were added dropwise (as a solution in 0.5 ml of methylene chloride). The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days, then treated with 5 ml of 1N sodium hydroxide solution, left to warm to room temperature and stirred for 1 hour. The phases were then separated, the aqueous phase was washed twice with methylene chloride, the organic phases were dried over sodium sulphate and concentrated. The colourless oil obtained was dissolved in 20 ml of ethyl ether and stirred with 5 ml of 1N sodium hydroxide solution for 1 hour. The phases were again separated, the aqueous phase was washed twice with ethyl ether, the organic phases were dried over sodium sulphate and concentrated. There were obtained 188 mg (98%) of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol. the mixture was left The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days left The phases were then separated the aqueous phase was washed twice with methylene chloride the organic phases were dried over sodium sulphate concentrated The colourless oil obtained The phases were again separated the aqueous phase was washed twice with ethyl ether the organic phases were dried over sodium sulphate concentrated

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

Procedure: d-Tartaric acid (25 g, 167 mmol), n-butanol (200 mL) and concentrated H2SO4 (59 mL) were heated under reflux overnight. The solution was cooled to room temperature then partitioned between H2O and CH2Cl2. The organic layer was washed with aqueous saturated NaHCO3 then filtered through Celite. The organic solution was then washed with brine, dried (MgSO4), filtered, and the solvent removed in vacuo. The resulting oil was purified by Kugelrohr distillation (bp=100-105° C., 0.06 mm Hg) to yield 38 as a clear light yellow oil: 1H NMR (300 MHz, CDCl3) δ0.9 (t, 6H), 1.4 (m, 4H), 1.65 (m, 4H), 3.2 (m, 2H), 4.35 (m, 4H), 4.5 (m, 2H). under reflux overnight then partitioned between H2O and CH2Cl2 The organic layer was washed with aqueous saturated NaHCO3 then filtered through Celite The organic solution was then washed with brine dried (MgSO4) filtered the solvent removed in vacuo The resulting oil was purified by Kugelrohr distillation (bp=100-105° C., 0.06 mm Hg)

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

Procedure: 0.594 ml of titanium tetraisopropoxide was dissolved in 10 ml of dry methylene chloride. Thereupon, 524 mg of dibutyl D-tartrate were added dropwise at -20° C. and the mixture was left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol were then added and subsequently a further 180 mg of tert.butyl hydroperoxide (80%) were added dropwise (as a solution in 0.5 ml of methylene chloride). The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days, then treated with 5 ml of 1N sodium hydroxide solution, left to warm to room temperature and stirred for 1 hour. The phases were then separated, the aqueous phase was washed twice with methylene chloride, the organic phases were dried over sodium sulphate and concentrated. The colourless oil obtained was dissolved in 20 ml of ethyl ether and stirred with 5 ml of 1N sodium hydroxide solution for 1 hour. The phases were again separated, the aqueous phase was washed twice with ethyl ether, the organic phases were dried over sodium sulphate and concentrated. There were obtained 188 mg (98%) of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol. the mixture was left The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days left The phases were then separated the aqueous phase was washed twice with methylene chloride the organic phases were dried over sodium sulphate concentrated The colourless oil obtained The phases were again separated the aqueous phase was washed twice with ethyl ether the organic phases were dried over sodium sulphate concentrated

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

Procedure: 0.594 ml of titanium tetraisopropoxide is dissolved in 10 ml of dry methylene chloride. Thereupon, 524 ml of dibutyl D-tartrate are added dropwise at -20° C. and the mixture is left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol are then added and subsequently 180 mg of tert.butyl hydroperoxide (80%) are added dropwise (as a solution in 0.5 ml of methylene chloride). The thus-obtained yellow solution is left to stand at -20° C. for 4 to 5 days, then treated with 5 ml of 1N sodium hydroxide solution, left to warm to room temperature and stirred for 1 hour. The phases are then separated, and the aqueous phase is washed twice with methylene chloride. The combined organic phases are subsequently dried over anhydrous sodium sulphate and concentrated. The thus-obtained colourless oil is dissolved in 20 ml of diethyl ether and stirred with 5 ml of 1N sodium hydroxide solution for 1 hour. The phases are again separated, the aqueous phase is washed twice with diethyl ether and the organic phases are dried over anhydrous sodium sulphate and concentrated. There are obtained 188 mg (98%) of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol, [α]D20 +18.2° (c=2% in CHCl3). the mixture is left The thus-obtained yellow solution is left to stand at -20° C. for 4 to 5 days left The phases are then separated the aqueous phase is washed twice with methylene chloride The combined organic phases are subsequently dried over anhydrous sodium sulphate concentrated The thus-obtained colourless oil is dissolved in 20 ml of diethyl ether stirred with 5 ml of 1N sodium hydroxide solution for 1 hour The phases are again separated the aqueous phase is washed twice with diethyl ether the organic phases are dried over anhydrous sodium sulphate concentrated

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

Procedure: 0.594 ml of titanium tetraisopropoxide was dissolved in 10 ml of dry methylene chloride. Thereupon, 524 mg of dibutyl D-tartrate were added dropwise at -20° C. and the mixture was left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol were then added and subsequently a further 180 mg of tert.butyl hydroperoxide (80%) were added dropwise (as a solution in 0.5 ml of methylene chloride). The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days, then treated with 5 ml of 1N sodium hydroxide solution, left to warm to room temperature and stirred for 1 hour. The phases were then separated, the aqueous phase was washed twice with methylene chloride, the organic phases were dried over sodium sulphate and concentrated. The colourless oil obtained was dissolved in 20 ml of ethyl ether and stirred with 5 ml of 1N sodium hydroxide solution for 1 hour. The phases were again separated, the aqueous phase was washed twice with ethyl ether, the organic phases were dried over sodium sulphate and concentrated. There were obtained 188 mg (98%) of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol. [α]D20 +18.2° (c=2% in chloroform). the mixture was left The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days left The phases were then separated the aqueous phase was washed twice with methylene chloride the organic phases were dried over sodium sulphate concentrated The colourless oil obtained The phases were again separated the aqueous phase was washed twice with ethyl ether the organic phases were dried over sodium sulphate concentrated

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

Procedure: d-Tartaric acid (25 g, 167 mmol), n-butanol (200 mL) and concentrated H2SO4 (59 mL) were heated under reflux overnight. The solution was cooled to room temperature then partitioned between H2O and CH2Cl2. The organic layer was washed with aqueous saturated NaHCO3 then filtered through Celite. The organic solution was then washed with brine, dried (MgSO4), filtered, and the solvent removed in vacuo. The resulting oil was purified by Kugelrohr distillation (bp=100-105° C., 0.06 mm Hg) to yield 38 as a clear light yellow oil: 1H NMR (300 MHz, CDCl3) δ0.9 (t, 6H), 1.4 (m, 4H), 1.65 (m, 4H), 3.2 (m, 2H), 4.35 (m, 4H), 4.5 (m, 2H). under reflux overnight then partitioned between H2O and CH2Cl2 The organic layer was washed with aqueous saturated NaHCO3 then filtered through Celite The organic solution was then washed with brine dried (MgSO4) filtered the solvent removed in vacuo The resulting oil was purified by Kugelrohr distillation (bp=100-105° C., 0.06 mm Hg)

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

Procedure: 0.594 ml of titanium tetraisopropoxide was dissolved in 10 ml of dry methylene chloride. Thereupon, 524 mg of dibutyl D-tartrate were added dropwise at -20° C. and the mixture was left to stand at -20° C. for 10 minutes. 197 mg of 4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-2-butenol were then added and subsequently a further 180 mg of tert.butyl hydroperoxide (80%) were added dropwise (as a solution in 0.5 ml of methylene chloride). The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days, then treated with 5 ml of 1N sodium hydroxide solution, left to warm to room temperature and stirred for 1 hour. The phases were then separated, the aqueous phase was washed twice with methylene chloride, the organic phases were dried over sodium sulphate and concentrated. The colourless oil obtained was dissolved in 20 ml of ethyl ether and stirred with 5 ml of 1N sodium hydroxide solution for 1 hour. The phases were again separated, the aqueous phase was washed twice with ethyl ether, the organic phases were dried over sodium sulphate and concentrated. There were obtained 188 mg (98%) of (2R,3R)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2,3-epoxy-2-methylbutanol. the mixture was left The thus-obtained yellow solution was left to stand at -20° C. for 4 to 5 days left The phases were then separated the aqueous phase was washed twice with methylene chloride the organic phases were dried over sodium sulphate concentrated The colourless oil obtained The phases were again separated the aqueous phase was washed twice with ethyl ether the organic phases were dried over sodium sulphate concentrated