Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

Provided are a method for efficiently producing an asymmetric conjugated diyne from an inexpensive and safe alternative compound to hydroxylamine hydrochloride and a method for producing a Z,Z-conjugated diene compound from the asymmetric conjugated diyne compound thus obtained. More specifically, provided is a method for producing an asymmetric conjugated diyne compound comprising a step of subjecting a terminal alkyne compound (1): HC≡C—Z.sup.1—Y.sup.1 to a coupling reaction with an alkynyl halide (2): Y.sup.2—Z.sup.2—C≡C—X by using sodium borohydride in water and an organic solvent in the presence of a copper catalyst and a base to obtain the asymmetric conjugated diyne compound (3): Y.sup.2—Z.sup.2—C≡C—C≡C—Z.sup.1—Y.sup.1. In addition, provided is a method for producing a Z,Z-conjugated diene compound by reducing the resulting asymmetric conjugated diyne compound, or the like.

Methods for the synthesis of a tricyclic-prostaglandin D.sub.2 metabolite methyl ester or a pharmaceutically acceptable salt thereof.

Methods for the synthesis of a tricyclic-prostaglandin D.sub.2 metabolite methyl ester or a pharmaceutically acceptable salt thereof.

The present invention discloses a novel method of preparing 8-methyldecanal, a flavor and fragrance material. Specifically, starting from cheap and readily available material 6-chloro-1-hexanol, first, the hydroxyl group was protected with dihydropyran catalyzed by para-toluene sulfonic acid to produce 6-chloro-hexyl tetrahydropyran ether. Then 6-chloro-hexyl tetrahydropyran ether reacted with magnesium turnings to form a Grignard reagent and reacted with 1-bromo-2-methyl-butane under the catalysis of cuprous bromide to give the intermediate 8-methyl-sunny tetrahydropyran ether. Without purification, crude 8-methyl-sunny tetrahydropyran ether was treated under acidic conditions to remove the protecting group to generate 8-methyl-1-decyl alcohol. Finally, 8-methyl decanal was obtained after oxidation with 2, 2, 6, 6-tetramethylpiperidinyloxy. The novel method of preparing 8-methyldecanal disclosed in the present invention utilizes common raw materials with low costs, the reaction conditions are mild, and yield is high. It is suitable for large-scale production.

The present invention discloses a novel method of preparing 8-methyldecanal, a flavor and fragrance material. Specifically, starting from cheap and readily available material 6-chloro-1-hexanol, first, the hydroxyl group was protected with dihydropyran catalyzed by para-toluene sulfonic acid to produce 6-chloro-hexyl tetrahydropyran ether. Then 6-chloro-hexyl tetrahydropyran ether reacted with magnesium turnings to form a Grignard reagent and reacted with 1-bromo-2-methyl-butane under the catalysis of cuprous bromide to give the intermediate 8-methyl-sunny tetrahydropyran ether. Without purification, crude 8-methyl-sunny tetrahydropyran ether was treated under acidic conditions to remove the protecting group to generate 8-methyl-1-decyl alcohol. Finally, 8-methyl decanal was obtained after oxidation with 2, 2, 6, 6-tetramethylpiperidinyloxy. The novel method of preparing 8-methyldecanal disclosed in the present invention utilizes common raw materials with low costs, the reaction conditions are mild, and yield is high. It is suitable for large-scale production.

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M 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 CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M 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 CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

Embodiments of a system and method are disclosed for obtaining high-energy fuels. In some embodiments, the system and method produces one or more fused cyclic compounds that can include one or more bridging points. The fused cyclic compounds are suitable for use as a high-energy fuels, and may be derived from biomass.

The present invention discloses a novel method of preparing 8-methyldecanal, a flavor and fragrance material. Specifically, starting from cheap and readily available material 6-chloro-1-hexanol, first, the hydroxyl group was protected with dihydropyran catalyzed by para-toluene sulfonic acid to produce 6-chloro-hexyl tetrahydropyran ether. Then 6-chloro-hexyl tetrahydropyran ether reacted with magnesium turnings to form a Grignard reagent and reacted with 1-bromo-2-methyl-butane under the catalysis of cuprous bromide to give the intermediate 8-methyl-sunny tetrahydropyran ether. Without purification, crude 8-methyl-sunny tetrahydropyran ether was treated under acidic conditions to remove the protecting group to generate 8-methyl-1-decyl alcohol. Finally, 8-methyl decanal was obtained after oxidation with 2, 2, 6, 6-tetramethylpiperidinyloxy. The novel method of preparing 8-methyldecanal disclosed in the present invention utilizes common raw materials with low costs, the reaction conditions are mild, and yield is high. It is suitable for large-scale production.