5-propan-2-ylbicyclo[3.1.0]hexan-2-one

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

Procedure: 25 ml of DMSO, 35 ml of benzene, 25 ml of isopropyl alcohol, 3.1 g (25 mM) of CP, 2.4 g (30 mM) of 50% aqueous sodium hydroxide and 5 ml of water were added to 6.9 g (31.25 mM) of trimethylsulfoxonium iodide and the reaction was carried out at room temperature for 5 hours. Then, the treatments were carried out as described in Example 8. 2.6 g (76% yield) of crude product were produced, from which1.45 g (42 % yield) of sabina ketone were obtained by distillation. 2.6 g (76% yield) of crude product were produced, from which1

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

Procedure: To a THF solution of lithium diisopropylamide prepared from 26 mM of diisopropylamine and 26 mM of n-butyllithium, 6.16 g (28 mM) of trimethylsulfoxonium iodide were added under ice cooling, and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. This reaction mixture was poured dropwise into a solution of 2.48 g (20 mM) of CP in 20 ml of THF during 4 hours. After the reaction was carried out at room temperature for 3 hours, the treatments were carried out as described in Example 8. 2.48 g (89% yield) of crude product were produced, from which 1.76 g (63% yield) of sabina ketone were obtained by distillation. were added under ice cooling at room temperature for 2 hours After the reaction was carried out at room temperature for 3 hours

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

Procedure: To a THF solution of lithium diisopropylamide prepared from 26 mM of diisopropylamine and 26 mM of n-butyllithium, 6.16 g (28 mM) of trimethylsulfoxonium iodide were added under ice cooling, and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. This reaction mixture was poured dropwise into a solution of 2.48 g (20 mM) of CP in 20 ml of THF during 4 hours. After the reaction was carried out at room temperature for 3 hours, the treatments were carried out as described in Example 8. 2.48 g (89% yield) of crude product were produced, from which 1.76 g (63% yield) of sabina ketone were obtained by distillation. were added under ice cooling at room temperature for 2 hours After the reaction was carried out at room temperature for 3 hours

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

Procedure: In the process, however, a relatively greater number of steps have to be pursued up to the course of synthesis of sabina ketone (6). In addition, since sabine ketone is obtainable from the starting material 3-isopropyl-2-cyclopenten-1-one only in about 57% yield, the total yield of sabinene hydrate results in lower value. Moreover, according to the process, operations and works are complicated and laborious, as it requires isolation procedures for each intermediate. Further, it is necessary to use valuable reagents and chromate compound hazardous in handling. Therefore, sabinene hydrates cannot be produced efficiently or economically, in particular, in large scale. Furthermore, by the process, cis-sabinene hydrate (formula 8) is produced preferentially and trans-sabinene hydrate (formula 7) appears only in a considerably minor amount. That is to say, a ratio of formation of trans-compound to cis-compound is 1:8.5, so that the process does not suit an industrial synthesis of trans-sabinene hydrate. Also, yield of trans- and cis-sabinene hydrates from sabina ketone is about 11%, and yield from 3-isopropyl-2-cyclopenten-1-one is about 6.3%.

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

Procedure: In the process, however, a relatively greater number of steps have to be pursued up to the course of synthesis of sabina ketone (6). In addition, since sabine ketone is obtainable from the starting material 3-isopropyl-2-cyclopenten-1-one only in about 57% yield, the total yield of sabinene hydrate results in lower value. Moreover, according to the process, operations and works are complicated and laborious, as it requires isolation procedures for each intermediate. Further, it is necessary to use valuable reagents and chromate compound hazardous in handling. Therefore, sabinene hydrates cannot be produced efficiently or economically, in particular, in large scale. Furthermore, by the process, cis-sabinene hydrate (formula 8) is produced preferentially and trans-sabinene hydrate (formula 7) appears only in a considerably minor amount. That is to say, a ratio of formation of trans-compound to cis-compound is 1:8.5, so that the process does not suit an industrial synthesis of trans-sabinene hydrate. Also, yield of trans- and cis-sabinene hydrates from sabina ketone is about 11%, and yield from 3-isopropyl-2-cyclopenten-1-one is about 6.3%.

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

Procedure: In the process, however, a relatively greater number of steps have to be pursued up to the course of synthesis of sabina ketone (6). In addition, since sabine ketone is obtainable from the starting material 3-isopropyl-2-cyclopenten-1-one only in about 57% yield, the total yield of sabinene hydrate results in lower value. Moreover, according to the process, operations and works are complicated and laborious, as it requires isolation procedures for each intermediate. Further, it is necessary to use valuable reagents and chromate compound hazardous in handling. Therefore, sabinene hydrates cannot be produced efficiently or economically, in particular, in large scale. Furthermore, by the process, cis-sabinene hydrate (formula 8) is produced preferentially and trans-sabinene hydrate (formula 7) appears only in a considerably minor amount. That is to say, a ratio of formation of trans-compound to cis-compound is 1:8.5, so that the process does not suit an industrial synthesis of trans-sabinene hydrate. Also, yield of trans- and cis-sabinene hydrates from sabina ketone is about 11%, and yield from 3-isopropyl-2-cyclopenten-1-one is about 6.3%.

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

Procedure: 25 ml of DMSO, 35 ml of benzene, 25 ml of isopropyl alcohol, 3.1 g (25 mM) of CP, 2.4 g (30 mM) of 50% aqueous sodium hydroxide and 5 ml of water were added to 6.9 g (31.25 mM) of trimethylsulfoxonium iodide and the reaction was carried out at room temperature for 5 hours. Then, the treatments were carried out as described in Example 8. 2.6 g (76% yield) of crude product were produced, from which1.45 g (42 % yield) of sabina ketone were obtained by distillation. 2.6 g (76% yield) of crude product were produced, from which1

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

Procedure: To a THF solution of lithium diisopropylamide prepared from 26 mM of diisopropylamine and 26 mM of n-butyllithium, 6.16 g (28 mM) of trimethylsulfoxonium iodide were added under ice cooling, and the mixture was stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. This reaction mixture was poured dropwise into a solution of 2.48 g (20 mM) of CP in 20 ml of THF during 4 hours. After the reaction was carried out at room temperature for 3 hours, the treatments were carried out as described in Example 8. 2.48 g (89% yield) of crude product were produced, from which 1.76 g (63% yield) of sabina ketone were obtained by distillation. were added under ice cooling at room temperature for 2 hours After the reaction was carried out at room temperature for 3 hours

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

Procedure: In the process, however, a relatively greater number of steps have to be pursued up to the course of synthesis of sabina ketone (6). In addition, since sabine ketone is obtainable from the starting material 3-isopropyl-2-cyclopenten-1-one only in about 57% yield, the total yield of sabinene hydrate results in lower value. Moreover, according to the process, operations and works are complicated and laborious, as it requires isolation procedures for each intermediate. Further, it is necessary to use valuable reagents and chromate compound hazardous in handling. Therefore, sabinene hydrates cannot be produced efficiently or economically, in particular, in large scale. Furthermore, by the process, cis-sabinene hydrate (formula 8) is produced preferentially and trans-sabinene hydrate (formula 7) appears only in a considerably minor amount. That is to say, a ratio of formation of trans-compound to cis-compound is 1:8.5, so that the process does not suit an industrial synthesis of trans-sabinene hydrate. Also, yield of trans- and cis-sabinene hydrates from sabina ketone is about 11%, and yield from 3-isopropyl-2-cyclopenten-1-one is about 6.3%.

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

Procedure: In the process, however, a relatively greater number of steps have to be pursued up to the course of synthesis of sabina ketone (6). In addition, since sabine ketone is obtainable from the starting material 3-isopropyl-2-cyclopenten-1-one only in about 57% yield, the total yield of sabinene hydrate results in lower value. Moreover, according to the process, operations and works are complicated and laborious, as it requires isolation procedures for each intermediate. Further, it is necessary to use valuable reagents and chromate compound hazardous in handling. Therefore, sabinene hydrates cannot be produced efficiently or economically, in particular, in large scale. Furthermore, by the process, cis-sabinene hydrate (formula 8) is produced preferentially and trans-sabinene hydrate (formula 7) appears only in a considerably minor amount. That is to say, a ratio of formation of trans-compound to cis-compound is 1:8.5, so that the process does not suit an industrial synthesis of trans-sabinene hydrate. Also, yield of trans- and cis-sabinene hydrates from sabina ketone is about 11%, and yield from 3-isopropyl-2-cyclopenten-1-one is about 6.3%.