An enzyme-mediated method for the production of 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan, the products of said method, and uses of said products.

An enzyme-mediated method for the production of 3a-ethyl-6,6,9a-trimethyldodecahydronaphtho[2,1-b]furan, the products of said method, and uses of said products.

Method for hydrogenating an ester with molecular hydrogen to the corresponding alcohols in the presence of a ruthenium complex (I), wherein said complex comprises a tridentate ligand L of the general formula (II) ##STR00001##
n and m are each independently 0 or 1, and the solid-dashed double lines represent a single or double bond, with the proviso that in the case of n=1 both solid-dashed double lines represent a single bond and m is 1, and in the case of n=0 one solid-dashed double line represents a single bond and the other solid-dashed double line represents a double bond, wherein in the case of a double bond on the side facing the phenyl ring m=1, in the case of a double bond on the side facing the pyridyl ring m=0, or both solid-dashed double lines represent a single bond and m is 1.

Method for hydrogenating an ester with molecular hydrogen to the corresponding alcohols in the presence of a ruthenium complex (I), wherein said complex comprises a tridentate ligand L of the general formula (II) ##STR00001##
n and m are each independently 0 or 1, and the solid-dashed double lines represent a single or double bond, with the proviso that in the case of n=1 both solid-dashed double lines represent a single bond and m is 1, and in the case of n=0 one solid-dashed double line represents a single bond and the other solid-dashed double line represents a double bond, wherein in the case of a double bond on the side facing the phenyl ring m=1, in the case of a double bond on the side facing the pyridyl ring m=0, or both solid-dashed double lines represent a single bond and m is 1.

The present invention relates to a process for preparing a mixture M1 of enol phosphate isomers devoid of (E,E) isomer and comprising at least 98% of (E,Z) isomer, at least 0.1% of (Z,Z) isomer and at least 0.1% of (Z,E) isomer, comprising bringing a mixture of isomers of said enol phosphate comprising a detectable amount of (E,E) isomer into contact with a hydrolysable dienophile in an organic solvent, followed by base hydrolysis of the medium obtained and elimination of the adduct formed, in order to obtain the mixture M1 devoid of (E,E) isomer.

The present invention relates to a process for preparing a mixture M1 of enol phosphate isomers devoid of (E,E) isomer and comprising at least 98% of (E,Z) isomer, at least 0.1% of (Z,Z) isomer and at least 0.1% of (Z,E) isomer, comprising bringing a mixture of isomers of said enol phosphate comprising a detectable amount of (E,E) isomer into contact with a hydrolysable dienophile in an organic solvent, followed by base hydrolysis of the medium obtained and elimination of the adduct formed, in order to obtain the mixture M1 devoid of (E,E) isomer.

Method for hydrogenating an ester with molecular hydrogen to the corresponding alcohols in the presence of a ruthenium complex (I), wherein said complex comprises a tridentate ligand L of the general formula (II)

##STR00001##

n and m are each independently 0 or 1, and the solid-dashed double lines represent a single or double bond, with the proviso that in the case of n=1 both solid-dashed double lines represent a single bond and m is 1, and in the case of n=0 one solid-dashed double line represents a single bond and the other solid-dashed double line represents a double bond, wherein in the case of a double bond on the side facing the phenyl ring m=1, in the case of a double bond on the side facing the pyridyl ring m=0, or both solid-dashed double lines represent a single bond and m is 1.

Method for hydrogenating an ester with molecular hydrogen to the corresponding alcohols in the presence of a ruthenium complex (I), wherein said complex comprises a tridentate ligand L of the general formula (II)

##STR00001##

n and m are each independently 0 or 1, and the solid-dashed double lines represent a single or double bond, with the proviso that in the case of n=1 both solid-dashed double lines represent a single bond and m is 1, and in the case of n=0 one solid-dashed double line represents a single bond and the other solid-dashed double line represents a double bond, wherein in the case of a double bond on the side facing the phenyl ring m=1, in the case of a double bond on the side facing the pyridyl ring m=0, or both solid-dashed double lines represent a single bond and m is 1.

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3). ##STR00001##

A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M.sup.1 represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X.sup.1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3). ##STR00001##