The invention includes procedures for stereoselective -acylation of carboxylic acids having a -carbon atom. For example, stereoselective acylation procedures include the following reactions: (I)

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The invention includes procedures for stereoselective -acylation of carboxylic acids having a -carbon atom. For example, stereoselective acylation procedures include the following reactions: (I)

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A method for producing a carbonyl compound represented by formula (1):

##STR00001##

wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2):

##STR00002##

wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

A method for producing a carbonyl compound represented by formula (1):

##STR00001##

wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2):

##STR00002##

wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

A method for producing a carbonyl compound represented by formula (1):

##STR00001##

wherein R.sup.1 is hydrogen or an organic group; R.sup.2 is hydrogen or an organic group; and R.sup.3 is hydrogen or an organic group; or two or three of R.sup.1, R.sup.2, and R.sup.3 may be linked to form a ring that may have at least one substituent, the method comprising step A of oxidizing an olefin compound represented by formula (2):

##STR00002##

wherein symbols are as defined above, by an oxidizing agent in the presence of (a) a non-alcohol organic solvent, (b) water, (c) a metal catalyst, and (d) an additive represented by the formula: MXn, wherein M is an element belonging to any one of Group 1, Group 2, Group 13, Group 14, and Group 15 in the periodic table, or NR.sub.4, wherein R is hydrogen or a C.sub.1-10 organic group; X is halogen; and n is a number of 1 to 5.

The present invention relates to the manufacturing of a process of alkyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and alkyl 2-acetyl-9,13-di-methyl-5-methylenetetradeca-8,12-dienoate as well as 6,10,14-trimethylpenta-deca-5,9,13-trien-2-one and 10,14-dimethyl-6-methylenepentadeca-9,13-dien-2-5 one and 6,10,14-trimethylpentadecan-2-one.

The present invention relates to the manufacturing of a process of alkyl 2-acetyl-5,9,13-trimethyltetradeca-4,8,12-trienoates and alkyl 2-acetyl-9,13-di-methyl-5-methylenetetradeca-8,12-dienoate as well as 6,10,14-trimethylpenta-deca-5,9,13-trien-2-one and 10,14-dimethyl-6-methylenepentadeca-9,13-dien-2-5 one and 6,10,14-trimethylpentadecan-2-one.

The present invention relates to a novel production method of a novel prostaglandin derivative or a pharmaceutically acceptable salt thereof useful as a medicament, and an intermediate therefor. According to the present invention, a production method of a novel prostaglandin derivative or a pharmaceutically acceptable salt thereof including a conversion step from a compound represented by the following formula 3 to a compound represented by the formula 1 can be provided:

##STR00001##

wherein each symbol is as defined in the DESCRIPTION.

The present invention relates to a novel production method of a novel prostaglandin derivative or a pharmaceutically acceptable salt thereof useful as a medicament, and an intermediate therefor. According to the present invention, a production method of a novel prostaglandin derivative or a pharmaceutically acceptable salt thereof including a conversion step from a compound represented by the following formula 3 to a compound represented by the formula 1 can be provided:

##STR00001##

wherein each symbol is as defined in the DESCRIPTION.

Methods for syntheses of organic acids from -keto acids, including methods for syntheses of isotopically encriched organic acids from -keto acids are disclosed. The isotopically enriched organic acids are useful, for example, in metabolic flux analyses.