3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran

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

Procedure: β-naphthyl ketone; benzyl acetone:mixture of hexahydro-4,7-methanoinden-5-yl propionate and hexahydro-4,7-methanoinden-6-yl propionate;4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-3-buten-2-one; 3,7-dimethyl-2,6-nonadien-1-nitrile; dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan; ethylene glycol cyclic ester of n-dodecanedioic acid; 1-cyclohexadecen-6-one; 1-cycloheptadecen-10-one; and corn mint oil.

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

Procedure: In this example, the ability of Ascomycete sp. KSM-JL2842 for producing a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate was examined. At the outset, a platinum loopful of Ascomycete sp. KSM-JL2842 was inoculated into 2.1% YM broth (Becton Dickinson), shake-culture was conducted at 25° C. for 2 days, and the resultants were designated as starter strains. Subsequently, the starter strains were inoculated into a medium containing 2.1% YM broth, 0.1% magnesium sulfate heptahydrate, 1% Tween 80, and 2% sclareol to a concentration of 2%, and shake culture was conducted at 25° C. The culture solution was subjected to extraction and GC analysis via the method of Example 1, and the amounts of the dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates to be produced were determined. The results are shown in Table 3. The units for the numerical values shown in Table 3 are “g/l.” was conducted at 25° C The culture solution was subjected to extraction and GC analysis via the method of Example 1

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

Procedure: Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (occasionally referred to as “Ambroxan (trademark)”) is an aroma chemical with satisfactorily long-lasting properties that is produced via chemical conversion mainly from sclareol extracted from Salvia sclarea. FIG. 1 shows a process for producing dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from sclareol. As shown in FIG. 1, decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol and sclareolide (decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one) are known as dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates. Also, a cyclic ether compound (8α,13-oxido-12,13-dehydro-15,16-dinorlabdane) is known as a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate, although it is not shown in FIG. 1.

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

Procedure: Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (occasionally referred to as “Ambroxan (trademark)”) is an aroma chemical with satisfactorily long-lasting properties that is produced via chemical conversion mainly from sclareol extracted from Salvia sclarea. FIG. 1 shows a process for producing dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from sclareol. As shown in FIG. 1, decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol and sclareolide (decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one) are known as dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates. Also, a cyclic ether compound (8α,13-oxido-12,13-dehydro-15,16-dinorlabdane) is known as a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate, although it is not shown in FIG. 1.

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

Procedure: In this example, the ability of Ascomycete sp. KSM-JL2842 for producing a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate was examined. At the outset, a platinum loopful of Ascomycete sp. KSM-JL2842 was inoculated into 2.1% YM broth (Becton Dickinson), shake-culture was conducted at 25° C. for 2 days, and the resultants were designated as starter strains. Subsequently, the starter strains were inoculated into a medium containing 2.1% YM broth, 0.1% magnesium sulfate heptahydrate, 1% Tween 80, and 2% sclareol to a concentration of 2%, and shake culture was conducted at 25° C. The culture solution was subjected to extraction and GC analysis via the method of Example 1, and the amounts of the dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates to be produced were determined. The results are shown in Table 3. The units for the numerical values shown in Table 3 are “g/l.” was conducted at 25° C The culture solution was subjected to extraction and GC analysis via the method of Example 1

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

Procedure: Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (occasionally referred to as “Ambroxan (trademark)”) is an aroma chemical with satisfactorily long-lasting properties that is produced via chemical conversion mainly from sclareol extracted from Salvia sclarea. FIG. 1 shows a process for producing dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from sclareol. As shown in FIG. 1, decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol and sclareolide (decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one) are known as dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates. Also, a cyclic ether compound (8α,13-oxido-12,13-dehydro-15,16-dinorlabdane) is known as a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate, although it is not shown in FIG. 1.

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

Procedure: β-naphthyl ketone; benzyl acetone:mixture of hexahydro-4,7-methanoinden-5-yl propionate and hexahydro-4,7-methanoinden-6-yl propionate;4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-methyl-3-buten-2-one; 3,7-dimethyl-2,6-nonadien-1-nitrile; dodecahydro-3a,6,6,9a-tetramethylnaphtho(2,1-b)furan; ethylene glycol cyclic ester of n-dodecanedioic acid; 1-cyclohexadecen-6-one; 1-cycloheptadecen-10-one; and corn mint oil.

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

Procedure: In this example, the ability of Ascomycete sp. KSM-JL2842 for producing a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate was examined. At the outset, a platinum loopful of Ascomycete sp. KSM-JL2842 was inoculated into 2.1% YM broth (Becton Dickinson), shake-culture was conducted at 25° C. for 2 days, and the resultants were designated as starter strains. Subsequently, the starter strains were inoculated into a medium containing 2.1% YM broth, 0.1% magnesium sulfate heptahydrate, 1% Tween 80, and 2% sclareol to a concentration of 2%, and shake culture was conducted at 25° C. The culture solution was subjected to extraction and GC analysis via the method of Example 1, and the amounts of the dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates to be produced were determined. The results are shown in Table 3. The units for the numerical values shown in Table 3 are “g/l.” was conducted at 25° C The culture solution was subjected to extraction and GC analysis via the method of Example 1

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

Procedure: Dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan (occasionally referred to as “Ambroxan (trademark)”) is an aroma chemical with satisfactorily long-lasting properties that is produced via chemical conversion mainly from sclareol extracted from Salvia sclarea. FIG. 1 shows a process for producing dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan from sclareol. As shown in FIG. 1, decahydro-2-hydroxy-2,5,5,8a-tetramethylnaphthaleneethanol and sclareolide (decahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan-2(1H)-one) are known as dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediates. Also, a cyclic ether compound (8α,13-oxido-12,13-dehydro-15,16-dinorlabdane) is known as a dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan intermediate, although it is not shown in FIG. 1.