Sagami Chemical Research Center

Sumitomo Chemical Company, Limited

Other

Kyorin Pharmaceutical Co., Ltd.

Kowa Company Limited

Sumitomo Pharmaceuticals Company Limited

Kuraray Co., Ltd.

Shiro Terashima

Yasumichi Fukuda

Kenji Koga

Katsuji Ujita

Katsumi Tamoto

Yasuo Oomori

Yoshikazu Kimura

Norihiko Tanno

Tamejiro Hiyama

Masahiko Nagakura

Kunikazu Sakai

Tomoya Kuwayama

Munehiko Nara

Kazuya Shimizu

Yoshio Ito

Akihiro Ishiwata

Makoto Sunagawa

Kenji Hirai

Kiyosi Kondo

Koichi Kanehira

Akira Sasaki

Shigeki Seto

Masanori Takadoi

Takashi Sugioka

Naganori Numao

Masamichi Sugimori

Yasuhisa Asano

Hiroyuki Ebisu

Tadashi Katoh

Shun-Ichi Yamada

Shun-ichi Yamada

Rumiko Shimazawa

Teruyo Matsumoto

Michiyo Suzuki

Rumiko Abe

Kaori Endo

Akiko Nakazawa

Takeo Kawabata

Etsuko Itoh

Norio Shibata

Process for the production of 5-oxy-7-oxabicyclo &lsqb;4.1.0&rsqb; hept-3-ene-3-carboxylic acid esters

The present invention provides a method of producing 7-azabicyclo&lsqb;4.1.0&rsqb;hept-3-ene-3-carboxylic acid ester (VII) economically, industrially advantageously and efficiently in a large amount. The present invention relates to a production method of compound (VII), which includes reacting epoxide (I) with amine (II) to give aminodiol (III), reacting the aminodiol (III) with a sulfonylating agent in the presence of a base to give azabicyclohept-2-ene (IV), reacting the azabicyclohept-2-ene (IV) with alcohol (V) in the presence of a Lewis acid to give azabicyclohept-3-ene (VI), and eliminating the 7-position substituent R from the azabicyclohept-3-ene (VI)

Process for the preparation of 7-azabicyclo&lsqb;4.1.0&rsqb;hept-3-ene-3-carboxylic acid esters

Process for preparation of 7-oxabicyclo&lsqb;2.2.1&rsqb;hept-5-ene-2-carboxylic acid derivatives

Hydronaphtho&lsqb;2,3-c&rsqb;furan derivatives and process for the preparation thereof

Pyrroloindole derivatives and intermediates in producing the same

Intermediates for the preparation of duocarmycin SA and derivatives

3-Amino-2-hydroxy-4-phenylbutyronitrile derivatives represented by the formula (3) may be prepared by reacting an aminoaldehyde derivative represented by the formula (1) with a cyanohydrin derivative represented by the formula (2) in the presence of a metallic compound, base, or acid; ##STR1## wherein R.sup.1 and R.sup.2 each independently represents a hydrogen atom or a protective group for an amino group, R.sup.3 and R.sup.4 each represents an alkyl or cycloalkyl group or R.sup.3 and R.sup.4 together form a tetramethylene or pentamethylene group.

Process for the preparation of 3-amino-2-hydroxy-4-phenylbutyronitrile

Acrylamide derivatives and process for production thereof

Trifluoromethylpyrroloindolecarboxylic acid ester and process for

A compound of the formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each a hydrogen atom, a lower alkyl group, an ar(lower)alkyl group or an aryl group, or R.sub.1 and R.sub.2 may be combined together to form a lower alkylene group and/or R.sub.3 and R.sub.4 are combined together to form a lower alkylene group, or R.sub.1, R.sub.2, R.sub.3 and R.sub.4 may be combined together to form an o-phenylene group, X is a halogen atom and Y is an oxygen atom or a nitrogen atom substituted with lower alkyl or aryl, which is useful as an intermediate in the synthesis of 1.beta.-methylcarbapenem compounds valuable as antibiotics.

Heterocyclic compounds and their production

An amino acid derivative of the formula: ##STR1## wherein R.sup.1 is a protective group for hydroxyl, which is useful as an intermediate for production of antimicrobial agent.

Amino acid derivatives, and their production

New L-phenylalanine dehydrogenases produced by a microorganism belonging to the genus Sporosarcina or Bacillus, new microorganisms capable of l-phenylalanine dehydrogenase and belonging to the genus Sporosarcina or Bacillus, a process for production of L-phenylalanine dehydrogenase using the microorganisms, and processes for production of L-amino acids using the enzymes or the microorganisms.

L-phenylalanine dehydrogenase and use thereof

A process for producing an anthracycline derivative represented by the general formula: ##STR1## where R.sup.1 is an acyl group, each of X.sup.1 and X.sup.2 is a hydrogen atom, a methoxy group, a hydroxyl group, a halogen atom or a lower alkyl group, each of Y.sup.1 and Y.sup.2 is a hydrogen atom, an alkoxy group or a hydroxyl group, and Z is a hydrogen atom or a protected hydroxyl group, which comprises reacting an anthracyclinone derivative represented by the general formula: ##STR2## where R is a hydrogen atom or a trialkylsilyl group, and X.sup.1, X.sup.2, Y.sup.1, Y.sup.2 and Z are as defined above, with a 1-acyl-sugar derivative represented by the general formula: ##STR3## where R.sup.2 is an acyl group and R.sup.1 is as defined above, in the presence of a silyl sulfonic acid derivative represented by the general formula:

Process for an anthracycline derivative, and an anthracyclinone

A process for preparing racemic 4-demethoxy-7-deoxydaunomycinone which comprises methylating an optically active .alpha.-hydroxyketone to give the corresponding methylated product of either one of the formulas: ##STR1## and reacting the latter with an acid to give a racemate of the .alpha.-hydroxyketone of the formula: ##STR2## .

Preparation of optically active 4-demethoxydaunomycinone

A process for preparing optically active 4-demethoxy-7-deoxydaunomycinone which comprises reacting a racemic mixture of the .alpha.-hydroxyketone of the formula: ##STR1## with an optical isomer of the .alpha.-glycol of the formula: ##STR2## wherein R is a group of the formula: ##STR3## and X is a halogen atom or a lower alkyl group to give a diastereomeric mixture of the acetal of the formula: ##STR4## .

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Tokyo, Japan

Shiro Terashima