Sumitomo Chemical Company, Limited

Sumitomo Electric Company, Limited

Takaharu Ikeda

Masayoshi Minai

Seiichi Kai

Kazuhiro Tada

Naohito Ohashi

Kikuo Ishizumi

Kozo Shimago

Gohfu Suzukamo

Yukio Yoneyoshi

Yoshiaki Oda

Hiroshi Yamachika

Naoto Konya

Hideyuki Ikehira

Haruki Morino

Sachiko Imazu

Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is H or C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:

Process for preparing haloketo acid derivatives

Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:

An improved process for preparing an optically active 4-hydroxycyclopentenone of the formula: ##STR1## wherein R is a lower alkyl, the symbol  means double bond or triple bond, and the * marked carbon is an asymmetric carbon, and the corresponding racemic 4-hydroxycyclopentenone, which are useful as an intermediate for preparing medicinal or agricultural products, particularly pharmaceutically active prostaglandins, and intermediates for preparing the optically active and/or racemic 4-hydroxycyclopentenone.

Process for preparing optically active cyclopentenones

The process for producing an optically active alcohol of the present invention comprises allowing

Process for producing optically active alcohol

A process for producing an optically active .alpha.-isopropyl-p-chlorophenylacetic acid (ICPA) of the formula: ##STR1## wherein the symbol * stands for an asymmetric carbon atom.

Process for producing an optically active

A triazole compound of the formula: ##STR1## wherein X is a hydrogen atom or a chlorine atom, which can be produced by subjecting an aromatic aldehyde of the formula: ##STR2## wherein X is as defined above, an alpha-halopinacolone of the formula: ##STR3## wherein Hal is a chlorine atom or a bromine atom and 1,2,4-triazole to condensation in the presence of an alkali, is useful as an intermediate in the synthesis of anti-microbial triazole-alcohols with high purity and high yield.

Triazole compounds, and their production

A novel process for preparing E-isomer of a triazolyl styryl ketone derivative of the formula (I): ##STR1## which includes treating Z-isomer of the derivative (which may contain E-isomer of the derivative) with sulfuric acid and an isomerization catalyst in an organic solvent, precipitating and separating the resulting sulfuric acid salt of E-isomer from the solution, and decomposing the resulting precipitate to obtain E-isomer of the derivative free from sulfuric acid. The E-isomer is useful for preparing E-isomer of triazolyl styryl carbinol of the formula (II): ##STR2## which is useful as an antimicrobial agent, a herbicide, a plant growth regulator, or the like.

Process for preparing E-isomer of a triazolyl styryl ketone derivative

A novel process for preparing the E-isomer of triazolyl styryl ketone derivative of the formula (I): ##STR1## is disclosed. The process includes treating the Z-isomer of the derivative which may contain the E-isomer of the derivative with an acid and an isomerization catalyst in an organic solvent, precipitating and separating the resulting salt of E-isomer from the solution, and decomposing the resulting precipitate to obtain the E-isomer of the derivative free from the acid. The E-isomer is useful for preparing the E-isomer of triazolyl styryl carbinol of the formula (II): ##STR2## which is useful as an antimicrobial agent, a herbicide, a plant growth regulator, or the like.

Process for preparing E-isomer of triazolyl styryl ketone derivative

A process for preparing an optically active cis-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione of the formula: ##STR1## wherein an asterisk (*) indicates an asymmetric carbon, Bzl represents a benzyl group and the 3a- and 6a-positions take the cis-configuration, which comprises reducing selectively an optically active cis-imidazolidinedicarboxylic acid monoester of the formula: ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group and Bzl is as defined above with a reducing agent at either one of the carboxyl group and the alkoxycarbonyl group in the said monoester, followed by cyclization.

Preparation of optically active

A process for preparing an optically active cis-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione of the formula: ##STR1## wherein an asterisk (*) indicates an asymmetric carbon, Bzl represents a benzyl group and the 3a- and 6a-positions take the cis-configuration, which comprises reducing selectively an optically active cis-imidazolidinedicarboxylic acid monoester of the formula: ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group and Bzl is as defined above with a reducing agent at either one of the carboxyl group and the alkoxycarbonyl group in the said monoester, followed by cyclization, the said monoester being the one obtainable by hydrolysis of a cis-imidazolidinedicarboxylic acid diester of the formula: ##STR3## wherein R and Bzl are each as defined above with an enzymatic material having a capability of hydrolyzing the ester group in the said diester.

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Ibaraki, Japan

Takaharu Ikeda