Process for the alkoxycarbonylation of trivinylcyclohexane.

Process for the alkoxycarbonylation of trivinylcyclohexane.

The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1).

##STR00001##

The present invention provides (6Z,9Z)-6,9-dodecadien-1-yne of the following formula (1). Further, the present invention provides a process for preparing (6Z,9Z)-6,9-dodecadien-1-yne (1): the process comprising reacting a (3Z,6Z)-10-halo-3,6-decadiene compound of the following general formula (2), wherein X represents a halogen atom with a metal acetylide of the following general formula (3), wherein M represents Na, Li, K, Ag, Cu (I), MgZ, CaZ, or Cu(II)Z, wherein Z represents a halogen atom or an ethinyl group to form (6Z,9Z)-6,9-dodecadien-1-yne (1).

##STR00001##

The invention relates to a method for catalytically producing an alkyl formate, wherein at least one alpha-hydroxy aldehyde, at least one alpha-hydroxy carboxylic acid, at least one carbohydrate, and/or at least one glycoside is reacted by means of a vanadium-oxygen compound, which contains vanadium in the oxidation stage +IV or +V, or a salt thereof as a catalyst in the solution, wherein the solution contains an alkanol, and the alkyl formate produced as a reaction product is separated from at least one other resulting reaction product. The catalyst which is reduced during the catalytic reaction is restored to its starting state in an oxidation process.

The invention relates to a method for catalytically producing an alkyl formate, wherein at least one alpha-hydroxy aldehyde, at least one alpha-hydroxy carboxylic acid, at least one carbohydrate, and/or at least one glycoside is reacted by means of a vanadium-oxygen compound, which contains vanadium in the oxidation stage +IV or +V, or a salt thereof as a catalyst in the solution, wherein the solution contains an alkanol, and the alkyl formate produced as a reaction product is separated from at least one other resulting reaction product. The catalyst which is reduced during the catalytic reaction is restored to its starting state in an oxidation process.

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 synthesizing amooranin (25-hydroxy-3-oxoolean-12-en-28-oic acid (AMR) and/or amooranin analogs, including amooranin methyl ester (AMR-Me), by using oleanolic acid in an oxidation process, and therapeutic uses thereof are described.

Methods for synthesizing amooranin (25-hydroxy-3-oxoolean-12-en-28-oic acid (AMR) and/or amooranin analogs, including amooranin methyl ester (AMR-Me), by using oleanolic acid in an oxidation process, and therapeutic uses thereof are described.