1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol

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

Procedure: 2,6-dimethyl-2,6-undecadiene-10-one; 2-methyl-5-isopropyl acetophenone; 2-hydroxy-2,5,5,8a-tetramethyl-1-(2-hydroxyethyl)-decahydronaphthalene;

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

Procedure: 2,6-dimethyl-2,6-undecadiene-10-one; 2-methyl-5-isopropyl acetophenone; 2-hydroxy-2,5,5,8a-tetramethyl-1-(2-hydroxyethyl)-decahydronaphthalene;

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

Procedure: 2,6-dimethyl-2,6-undecadiene-10-one; 2-methyl-5-isopropyl acetophenone; 2-hydroxy-2,5,5,8a-tetramethyl-1-(2-hydroxyethyl)-decahydronaphthalene;

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

Procedure: Four flasks, each containing an aqueous solution (100 mL) of 0.1% NH4NO3, 0.1% H2KPO4, 0.05% MgSO4.7H2O, trace minerals, and Vitamin B complex were sterilized at 120° C. for 20 minutes. A 50% aqueous solution of dextrose (5 mL) and Tween-80 (0.1 mL), containing Sclareol (4) (10 mg) was added to each flask. Each flask was inoculated with 5% by volume of three days grown cells CBS 214.83 (ATCC 20624). The cultures were then incubated at 25±1° C. on a rotary shaker (200 rpm) for 3 to 4 days. After the initial incubation period a mixture of Sclareol dissolved in Tween-80 (8.0 g) was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days. At the end of the incubation period the contents of the four flasks were combined, extracted with ethyl acetate (3×200 mL) and dried (Na2SO4). Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform to provide decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol (3) (2.4 g), mp 130.5°-131.5° C., (lit. 132°-133° C.) GLC purity 100%, H-NMR (CDCl3) δ0.79 (6H, 2s), 0.87 (3H, 2), (3H, 2), 0.9-20 (16H, m), 3.41-3.49 (1H, m), 3.72-3.79 (1H, m). IR (CHCl3) νmax, 3580, 3360, 2950, 1460, 1380 cm. MS m/e 236, 221, 117, 137, 109. [α]22D =-16.8° (CHCl3). [Literature 132°-133° C., [α]D22.5 =-17.3° (CHCl3).] [See M. Stoll and M. Hinder Helv. Chim. Acta (1953) 36 1955-2008.] was added to each flask Each flask was inoculated with 5% by volume of three days was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days extracted with ethyl acetate (3×200 mL) dried (Na2SO4) Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform

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

Procedure: Four flasks, each containing an aqueous solution (100 mL) of 0.1% NH4NO3, 0.1% H2KPO4, 0.05% MgSO4.7H2O, trace minerals, and Vitamin B complex were sterilized at 120° C. for 20 minutes. A 50% aqueous solution of dextrose (5 mL) and Tween-80 (0.1 mL), containing Sclareol (4) (10 mg) was added to each flask. Each flask was inoculated with 5% by volume of three days grown cells CBS 214.83 (ATCC 20624). The cultures were then incubated at 25±1° C. on a rotary shaker (200 rpm) for 3 to 4 days. After the initial incubation period a mixture of Sclareol dissolved in Tween-80 (8.0 g) was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days. At the end of the incubation period the contents of the four flasks were combined, extracted with ethyl acetate (3×200 mL) and dried (Na2SO4). Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform to provide decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol (3) (2.4 g), mp 130.5°-131.5° C., (lit. 132°-133° C.) GLC purity 100%, H-NMR (CDCl3) δ0.79 (6H, 2s), 0.87 (3H, 2), (3H, 2), 0.9-20 (16H, m), 3.41-3.49 (1H, m), 3.72-3.79 (1H, m). IR (CHCl3) νmax, 3580, 3360, 2950, 1460, 1380 cm. MS m/e 236, 221, 117, 137, 109. [α]22D =-16.8° (CHCl3). [Literature 132°-133° C., [α]D22.5 =-17.3° (CHCl3).] [See M. Stoll and M. Hinder Helv. Chim. Acta (1953) 36 1955-2008.] was added to each flask Each flask was inoculated with 5% by volume of three days was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days extracted with ethyl acetate (3×200 mL) dried (Na2SO4) Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform

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

Procedure: Four flasks, each containing an aqueous solution (100 mL) of 0.1% NH4NO3, 0.1% H2KPO4, 0.05% MgSO4.7H2O, trace minerals, and Vitamin B complex were sterilized at 120° C. for 20 minutes. A 50% aqueous solution of dextrose (5 mL) and Tween-80 (0.1 mL), containing Sclareol (4) (10 mg) was added to each flask. Each flask was inoculated with 5% by volume of three days grown cells CBS 214.83 (ATCC 20624). The cultures were then incubated at 25±1° C. on a rotary shaker (200 rpm) for 3 to 4 days. After the initial incubation period a mixture of Sclareol dissolved in Tween-80 (8.0 g) was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days. At the end of the incubation period the contents of the four flasks were combined, extracted with ethyl acetate (3×200 mL) and dried (Na2SO4). Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform to provide decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol (3) (2.4 g), mp 130.5°-131.5° C., (lit. 132°-133° C.) GLC purity 100%, H-NMR (CDCl3) δ0.79 (6H, 2s), 0.87 (3H, 2), (3H, 2), 0.9-20 (16H, m), 3.41-3.49 (1H, m), 3.72-3.79 (1H, m). IR (CHCl3) νmax, 3580, 3360, 2950, 1460, 1380 cm. MS m/e 236, 221, 117, 137, 109. [α]22D =-16.8° (CHCl3). [Literature 132°-133° C., [α]D22.5 =-17.3° (CHCl3).] [See M. Stoll and M. Hinder Helv. Chim. Acta (1953) 36 1955-2008.] was added to each flask Each flask was inoculated with 5% by volume of three days was added in portions during the next 5 days, afterwhich the incubation was continued for a further 4 days extracted with ethyl acetate (3×200 mL) dried (Na2SO4) Evaporation of the solvent provided a crude extract (4.0 g), which was crystallized from hexane/chloroform

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

Procedure: Isomerization and subsequent lithium alanate reduction of sclareolide by the method of G. Ohloff, Helv. Chim Acta, 68 (1985), 2022-29, was used to obtain a diastereoisomeric decahydro-2-hydroxy-2,5,5,8a-tetramethyl1-naphthaleneethanol (mp. 191° C.). 142 g of this diol were dissolved in 2,110 g of toluene, and the solution was admixed with 120 g (3 mol) of sodium hydroxide in 120 ml of water and then with 48 g (0.15 mol) of tetrabutylammonium bromide. 101 g (0.5 mol) of p-toluenesulfonyl chloride were then added twice in the course of 1 hour, and the reaction mixture was subsequently stirred for 2 hours, and admixed with 500 ml of water and thereafter thoroughly stirred for a further 10-20 minutes. The bottom, aqueous phase was separated off and washed once with 200 ml of water, and thereafter the solvent was distilled off at 300 mbar. Recrystallization of the residue left 121.6 g of isomeric dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (formula Ib; R1, R2 =CH3), of mp. 60° C. and [a]20D =+7.5°, which corresponds to a yield of 92%.