Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4)
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1 Supplementary Note 1 : Chemical synthesis of (E/Z)-4,8-dimethylnona-2,7-dien-4-ol (4) A solution of propenyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and 6-methylhept-5-en-2-one (15.8 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 5:1). Finally, 500 mg of trans-(e)-4 and 180 mg of cis-(z)-4 were isolated with yields of 20 % and 7 %, respectively. 1 H NMR of trans-(e)-4 (250 MHz, CDCl 3 ) = (m, 2H), (m, 1H), (m, 2H), (m, 3H), (m, 8H), 1.34 (s, 3H) ppm. 13C NMR (125 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm. 1 H NMR of cis-(z)-4 (250 MHz, CDCl 3 ) = (m, 2H), (m, 1H), (m, 2H), (m, 3H), (m, 8H), 1.26 (s, 3H) ppm. 13C NMR (125 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
2 Supplementary Note 2 : Chemical synthesis of 3-ethyloct-1-en-3-ol (6) A solution of vinyl magnesium bromide in THF (17.2 mmol) under nitrogen atmosphere was cooled in an ice bath and 2-octanone (15.6 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.3 g of 6 were isolated with a purity of 90 % (55% yield). 1 H NMR (250 MHz, CDCl 3 ) = 5.81 (dd, 1H), 5.15 (m, 2H), 1.52 (m, 4H), 1.39 (s, 1H), (m, 6H), 0.87 (m, 6H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), 7.73 (s) ppm.
3 Supplementary Note 3 : Chemical synthesis of (E)-3-methylocta-1,4-dien-3-ol (8) A solution of vinyl magnesium bromide in THF (19.6 mmol) under nitrogen atmosphere was cooled in an ice bath and hept-3-en-2-one (17.8 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.7 g of 8 were isolated with a purity of 90 % (68 % yield). 1 H NMR (250 MHz, CDCl 3 ) = (dd, J = 17.32, Hz, 1H), (m, 2H), (dd, J = 17.32, 1.22 Hz, 1H), (dd, J = 10.60, 1.22 Hz, 1H), (td, J = 7.14, 5.97, 5.97 Hz, 2H), 1.57 (d, J = 1.97 Hz, 1H), (m, 2H), 1.36 (s, 3H), 0.90 (t, 3H) ppm. 13 C NMR (125 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
4 Supplementary Note 4 : Chemical synthesis of 3-methylhex-1-en-3-ol (12) A solution of vinyl magnesium bromide in THF (20 mmol) under nitrogen atmosphere was cooled in an ice bath and 2-pentanone (18.4 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 480 mg of 12 were isolated with a purity of 90 % (23 % yield). 1 H-NMR (250 MHz, CDCl 3 ) δ = 5.91 (dd, J = 10.75, 17.5 Hz, 1H), 5.19 (dd, J = 1.25, 17.5 Hz, 1H), 5.04 (dd, 1H, J = 1.25, Hz, 1H), (m, 4H), 1.28 (s, 3H), 0.92 (t, 3H) ppm. 13 C-NMR (250 MHz, CDCl 3 ) δ = (s), (s), (s), (s), (s), (s), (s) ppm.
5 Supplementary Note 5 : Chemical synthesis of 3-methylhept-1-en-3-ol (14) A solution of vinyl magnesium bromide in THF (20 mmol) under nitrogen atmosphere was cooled in an ice bath and 2-hexanone (18.4 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.1 g of 14 were isolated with a purity of 90 % (47 % yield). 1 H-NMR (250 MHz, CDCl 3 ) δ = 5.91 (dd, J = 10.75, 17.5 Hz, 1H), 5.19 (dd, J = 1.25, 17.5 Hz, 1H), 5.04 (dd, 1H, J = 1.25, Hz, 1H), (m, 4H), 1.28 (s, 3H), 0.92 (t, 3H) ppm. 13 C-NMR (250 MHz, CDCl 3 ) δ = (s), (s), (s), (s), (s), (s), (s) ppm.
6 Supplementary Note 6 : Chemical synthesis of 3-methyl-5-phenylpent-1-en-3-ol (16) A solution of vinyl magnesium bromide in THF (14.9 mmol) under nitrogen atmosphere was cooled in an ice bath and 4-phenyl-2-butanone (13.5 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.74 g of 16 were isolated with a purity of 90 % (73 % yield). 1 H NMR (250 MHz, CDCl 3 ) = (m, 5H), (dd, 1H), (dd, 1H), (m, 1H), (m, 2H), (m, 2H), 1.35 (s, 3H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s,2c), (s,2c), (s), (s), (s), (s), (s), (s) ppm.
7 Supplementary Note 7 : Chemical synthesis of 3-methoxy-3,7-dimethylocta-1,6-diene (20) 1.5 g (37 mmol) of sodium hydride (57-63% dispersion in oil) was dissolved in 30 ml THF under nitrogen atmosphere at 0 C. 5 g (34 mmol) of linalool dissolved in 10 ml THF was slowly added under vigorous stirring while cooling. After 30 min 4.9 g methyl iodide (35 mmol) was slowly added to the mixture and stirred at room temperature overnight. The reaction was quenched with 50 ml water, the organic layer was separated and the water phase was extracted three times with 20 ml diethyl ether. The organic phases were collected and washed twice with brine. Removing of the solvent by evaporation followed flash chromatography purification of the crude product. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 3.74 g of 20 were isolated with a purity of 90 % (65 % yield). 1 H NMR (250 MHz, CDCl 3 ): (dd, 1H), (m, 3H), 3.16 (s, 3H), (dd, 2H), 1.68 (s, 3H), (m, 2H), 1.60 (s, 3H), 1.23 (s, 3H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
8 Supplementary Note 8 : Chemical synthesis of 2,6-dimethylhept-5-en-2-ol (23) A solution of methyl magnesium bromide in THF (17.4 mmol) under nitrogen atmosphere was cooled in an ice bath and 6-methylhept-5-en-2-one (15.8 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.36 g of 23 were isolated with a purity of 90% (61% yield). 1 H NMR (500 MHz, CDCl 3 ) = 5.14 (t, 1H), 2.07 (dd, 2H), 1.69 (s, 3H), 1.63 (s, 3H), (m, 2H), 1.23 (s, 6H) ppm. 13 C NMR (126 MHz, CDCl 3 ) = (s), (s), (s), (s), (s,2c), (s), (s), (s) ppm.
9 Supplementary Note 9 : Chemical synthesis of 3,7-dimethyl-6-octen-3-ol (24) A solution of ethyl magnesium bromide in THF (17.4 mmol) under nitrogen atmosphere was cooled in an ice bath and 6-methylhept-5-en-2-one (15.8 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.54 g of 24 were isolated with a purity of 90 % (68 % yield). 1 H NMR (250 MHz, CDCl 3 ) = (m, 1H), (dd, 2H), 1.69 (s, 3H), 1.63 (s, 3H), (m, 4H), 1.16 (s, 3H), (t, 3H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), 8.25 (s) ppm.
10 Supplementary Note 10 : Chemical synthesis of (E)-3-methyloct-4-en-3-ol (25) A solution of ethyl magnesium bromide in THF (19.6 mmol) under nitrogen atmosphere was cooled in an ice bath and hept-3-en-2-one (17.8 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.5 g of 25 were isolated with a purity of 90 % (59 % yield). 1 H NMR 300 MHz, CDCl 3 = 5.58 (m, 2H), 2.02 (dd, J = 13.76, 6.48 Hz, 2H), (m, 2H), (m, 2H), 1.25 (s, 3H), (2t, 6H) ppm. 13 C NMR (75 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
11 Supplementary Note 11 : Chemical synthesis of (E)-3,7-dimethylocta-1,4,6-trien-3-ol (26) A solution of vinyl magnesium bromide in THF (17.8 mmol) under nitrogen atmosphere was cooled in an ice bath and 6-methyl-3,5-heptadien-2-one (16.1 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 660 mg of 26 were isolated with a purity of 90% (27% yield). 1 H NMR (250 MHz, CDCl 3 ) = (dd, 1H, J = 10.9, 15.3 Hz), (dd, 1H, J = 10.6, 17.3 Hz), (d, 1H, J = 10.9 Hz), (d, 1H, J = 15.3 Hz), (dd, 1H, J = 1, 17.3 Hz), (dd, 1H, J = 1, 10.6 Hz), (2s, 6H), 1.4 (s, 3H) ppm. 13 C NMR (63 MHz, CDCl 3 ) (s), (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
12 Supplementary Note 12 : Chemical synthesis of (E)-3,7-dimethylocta-4,6-dien-3-ol (27) A solution of ethyl magnesium bromide in THF (17.7 mmol) under nitrogen atmosphere was cooled in an ice bath and 6-methylhepta-3,5-dien-2-one (16.1 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 950 mg of 27 were isolated with a purity of 90 % (38 % yield). 1 H NMR (250 MHz, CDCl 3 ) = 5.81 (dd, 1H), 5.15 (m, 2H), 1.52 (m, 4H), 1.39 (s, 1H), (m, 6H), 0.87 (m, 6H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), 7.73 (s) ppm.
13 Supplementary Note 13 : Chemical synthesis of 7-methylocta-1,6-dien-3-ol (28) Chemical synthesis of 28 is shown as a reaction scheme. The synthesis was performed according to literature. 4,5 The synthesis of 28 is achieved via the formation of intermediate product 1-bromo-4-methyl-3-pentene (32). 1-Bromo-4-methyl-3-pentene (32) To a solution of methylmagnesium bromide (62.5 mmol) in anhydrous THF (20 ml) under an inert atmosphere was addded dropwise a solution of cyclopropylmethyl ketone (31, 4.21 g, 50 mmol) in anhydrous THF (10 ml). The mixture was then heated to reflux for 20 min. on cooling to room temperature, the reaction mixture was slowly added to a cooled solution of concentrated sulfuric acid in water (1 :2, 35 ml). After addition stirring was contiuned for 30 min. The organic layer was then separated, the aqueous solution was extracted twice with diethyl ether (20 ml). After drying over MgSO 4, the solvent was removed under vacuum and the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 5.4 g of 32 were isolated with a purity of 90 % (56 % yield). 7-Methyl-1,6-octadien-3-ol (28) Magnesium tunings (1.1 g, 46 mmol) were stirred under inert atmosphere. Iodine crystals (5 mg) were added followed by anhydrous ether (30 ml). 1-Bromo-4-methylpent-3-ene (32, 5.4 g, 32 mmol) was dissolved in anhydrous ether (30 ml) and the solution added dropwise to the above suspension with heating. The mixture was then refluxed for 2 h and then cooled to - 15 C. Acrolein (2 g, 35 mmol) was added and the reaction stirred for 20 h at room temperature. The reaction mixture was then treated with saturated NH 4 Cl-solution (30 ml) and the organic layer separated. The aqueous solution was extracted twice with diethyl ether (20 ml) and the combined organic layers were washed with brine and dried (MgSO 4 ). After removal of the solvent under vacuum, the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 860 mg of 28 were isolated with a purity of 90 % (19 % yield). 1 H NMR (250 MHz, CDCl 3 ) = (m, 1H), (m, 3H), (q, 1H), (dd, 1H), 1.69 (s, 3H), 1.62 (s, 3H), (m, 2H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
14 Supplementary Note 14 : Chemical synthesis of 3,7-dimethylocta-1,6-dien-3-amine (linalyl amine 29) Chemical synthesis of 29 is shown as a reaction scheme. The synthesis was performed according to literature. 6 The synthesis of 29 is achieved via the formation of intermediate products geranioltrichloracetimidate (33) and 3,7-dimethyl-3-trichloracetamidoocta-1,6-diene (34). Geranioltrichloracetimidate (33) 410 mg (37 mmol) of sodium hydride (57-63% dispersion in oil) washed twice with 5 ml n- heptane and 60 ml of anhydrous ether was treated dropwise with a solution of 15.4 g (100 mmol) geraniol and 15 ml of anhydrous ether. After the evolution of hydrogen ceased, the reaction mixture was cooled to -10 C. Trichloroacetonitrile (10 ml, 100 mmol) was added dropwise to the stirred solution, while the temperature was maintained below 0 C. The solution was allowed to warm to room temperature and was concentrated. 150 ml n-pentane containing 0.4 ml (10 mmol) methanol was added and the mixture shaken vigorously for 1 min. Dark insoluble precipitation was removed by filtration. After washing the residue two times with n-pentane, the combined filtrated was concentrated to give 24 g (90 %) of 33. 3,7-Dimethyl-3-trichloracetamidoocta-1,6-diene (34) Crude imidate 33 (24 g) in 300 ml of xylene was heated at reflux for 8 h. after cooling to room temperature, the dark xylene solution was filtered through a short silica column (70 g) and toluene. The column was eluted with an additional 250 ml of toluene, and the combined light yellow eluent was concentrated and distilled through a Vigreux column to give 16 g (55 % for the two steps) of 34, bp C (13 mbar). 3,7-Dimethylocta-1,6-dien-3-amine (linalyl amine, 29) A solution of 16 g of trichloroacetamidodiene 34, 250 ml of 95 % ethanol and 200 ml of 6 N sodium hydroxide was stirred at room temperature for 48 h. Ether (300 ml) was added, the organic layer separated, and the aqueous layer washed twice with ether (50 ml). The combined extracts were dried (MgSO 4 ), concentrated and the semisolid residue extracted with 50 ml of boiling n-hexane. The hexane solution was concentrated and distilled through a Vigreoux column to yield 8 g (51 %) of 3,7-dimethylocta-1,6-dien-3-amine (linalyl amine, 29): bp C (14 mbar). 1 H NMR (500 MHz, CDCl 3 ) = 5.89 (dd, 1H), (m, 2H), 5.00 (dd, 1H), 1.95 (m, 2H), 1.67 (s, 3H), 1.59 (s, 3H), (m, 2H), 1.17 (s, 3H) ppm. 13 C NMR (126 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
15 Supplementary Note 15 : Chemical synthesis of 3,7-dimethyloct-6-en-1-yn-3-ol (30) A solution of ethinyl magnesium bromide in THF (17.5 mmol) under nitrogen atmosphere was cooled in an ice bath and 6-methylhept-5-en-2-one (15.8 mmol) dissolved in 10 ml THF was added slowly under vigorous stirring. After 1 hour stirring the mixture was allowed to warm up to room temperature for further 12 hours stirring. To quench the reaction a saturated ammonia chloride solution was added. The organic layer was separated and the water phase was extracted three times with 25 ml diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. After removing the solvent the residue was purified using column chromatography (cyclohexane/ethyl acetate 3:1). Finally, 1.85 g of 30 were isolated with a purity of 90 % (77 % yield). 1 H NMR (250 MHz, CDCl 3 ) = 5.17 (ddd, 1H), 2.46 (s, 1H), 1.70 (s, 3H), 1.68 (m, 4H), 1.66 (s, 3H), 1.50 (s, 3H) ppm. 13 C NMR (63 MHz, CDCl 3 ) = (s), (s), (s), (s), (s), (s), (s), (s), (s), (s) ppm.
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