(6R)-2,6-dimethylnon-2-ene

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

Procedure: To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated

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

Procedure: To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated

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

Procedure: To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give an oil. 32.6 g; 93%. Used without further purification. 13C NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60. After 10 hours the solution was cooled to 0° C. The resultant two layers were separated the aqueous phase extracted with ether The combined organic phases were dried (MgSO4) concentrated to give an oil Used without further purification

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

Procedure: To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated

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

Procedure: To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated

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

Procedure: To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give an oil. 32.6 g; 93%. Used without further purification. 13C NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60. After 10 hours the solution was cooled to 0° C. The resultant two layers were separated the aqueous phase extracted with ether The combined organic phases were dried (MgSO4) concentrated to give an oil Used without further purification

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

Procedure: To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated

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

Procedure: To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give an oil. 32.6 g; 93%. Used without further purification. 13C. NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60. After 10 hours the solution was cooled to 0° C. The resultant two layers were separated the aqueous phase extracted with ether The combined organic phases were dried (MgSO4) concentrated to give an oil Used without further purification

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

Procedure: To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give an oil. 32.6 g; 93%. Used without further purification. 13C. NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60. After 10 hours the solution was cooled to 0° C. The resultant two layers were separated the aqueous phase extracted with ether The combined organic phases were dried (MgSO4) concentrated to give an oil Used without further purification

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

Procedure: To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated

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

Procedure: To (S)-citronellyl bromide (50 g, 0.228 mol) in THF (800 mL) at 0° C. was added LiCl (4.3 g) followed by CuCl2 (6.8 g). After 30 minutes methylmagnesium chloride (152 mL of a 3 M solution in THF, Aldrich) was added and the solution warmed to room temperature. After 10 hours the solution was cooled to 0° C. and a saturated aqueous solution of ammonium chloride carefully added. The resultant two layers were separated and the aqueous phase extracted with ether. The combined organic phases were dried (MgSO4) and concentrated to give an oil. 32.6 g; 93%. Used without further purification. 13C NMR (100 MHz; CDCl3) 131.13, 125.28, 39.50, 37.35, 32.35, 25.92, 25.77, 20.31, 19.74, 17.81, 14.60. After 10 hours the solution was cooled to 0° C. The resultant two layers were separated the aqueous phase extracted with ether The combined organic phases were dried (MgSO4) concentrated to give an oil Used without further purification

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

Procedure: To (R)-2,6-dimethyl-non-2-ene (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave (R)-4-methyl-heptanoic acid as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%]. the solution extracted with ether The combined organic phases were dried (MgSO4) concentrated