Chisso Corporation

Asahi Denka Kogyo K.k.

Asahi Denka Kogyo Kabushiki Kaisha

Other

Nissan Chemical Industries Limited

Adeka Argus Chemical Co., Ltd.

Seiichi Takano

Kunio Ogasawara

Toshihiro Shibata

Norio Kurosawa

Masaki Kimura

Naoyuki Yoshida

Tetsuya Ogawa

Tsutomu Sugahara

Yohichi Shimazaki

Yoshinori Sekiguchi

The present invention relates to optically active cyclohexene diol derivatives and optically active cyclohexenone derivatives, and a process for production of these compounds in which a special cyclohexene diol of a starting material is reacted by selectively positioning transesterification in the presence of lipase to obtain an optically active cyclohexene diol derivative and then an optically active cyclohexenone derivative represented by the following formula: ##STR1## According to the present invention, optically active cyclohexene diol derivatives and optically-active cyclohexenone derivatives, which are intermediates for synthesizing physiologically active materials, can be obtained efficiently.

Cyclohexene diol derivatives

The present invention provides special epoxy derivative (1), cyclohexanone derivative (2), cyclohexenone derivative (3) and 3-substituted cyclohexenone derivative (4) which are useful as intermediates for synthesizing physiologically active materials, and a method for stereoselectively introducing substituted groups. Further, the present invention provides a method for synthesizing optically active compounds, such as optically active carvone via these intermediates. ##STR1##

Optically active compounds and a method for producing them

An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.

Optically active compounds and intermediates thereof, and process for

The present invention relates to optically active cyclohexene diol derivatives and optically active cyclohexenone derivatives, and a process for production of these compounds in which a special cyclohexene diol of a starting material is reacted by selectively positioning transesterification in the presence of lipase to obtain an optically active cyclohexene diol derivative and then an optically active cyclohexenone derivative represented by the following formula: ##STR1## According to the present invention, optically active cyclohexene diol derivatives and optically active cyclohexenone derivatives, which are intermediates for synthesizing physiologically active materials, can be obtained efficiently.

The present invention provides a method for producing (+)-estrone derivatives, characterized in that it comprises starting from a certain cyclopentadiene derivative, reacting the derivative with a certain diene compound by an asymmetric Diels-Alder reaction, and via intermediates obtaining a (+)-estron derivative represented by the following formula: ##STR1## wherein R is alkyl of 1-20 carbon atoms. According to the present invention, (+)-estron derivatives can be obtained by limited steps from the starting materials of dicyclopentadiene derivatives.

Method for producing (+)-estrone derivatives

An optically active compound of the formula (I): ##STR1## R is a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, an alkoxy group having 1 to 18 carbon atoms, --R' or --O--R' group; R' is a ##STR2## group, wherein Y is a halogen atom, a hydroxyl group, an alkoxy group having 1 to 18 carbon atoms or an acyloxy group having 1 to 18 carbon atoms; X is a direct bond or a ##STR3## group; m, n and p each are each 0 or 1, provided that at least one of m, n and p is 1; and , represents an asymetric carbon atom. The optically active compound can impart a desired helical pitch to a liquid crystal composition

Optically active compound

The present invention provides a process for producing an optically active cyclohexenone derivative characterized in that it comprises using a specialized cyclohexene derivative as a starting material, reacting the derivative with lipase by regioselective transesterification to obtain optically active cyclohexenone derivatives, represented by the following formulae. ##STR1##

Cyclohexene derivatives

A process for manufacturing an optically active saturated compound of the general formula (25): ##STR1## wherein R.sub.20 represents a group for protecting a hydroxy group, R.sub.21, R.sub.22, and R.sub.23 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, is disclosed.

Process for manufacture of optically active saturated compounds

The present invention is optically active epoxides and its production characterized in that the process comprises reacting alkenyl ethylene glycols with 0.5 to 2.0 equivalents of a titanium-tetraalkoxyde, a peroxide and an L-(+)- or D-(-)-dialkyl tartrate at a temperature of -78.degree. to 50.degree. C. to asymmetrically oxidize the alkenyl ethylene glycols. The production of the present invention is an excellent method for producing chiral epoxides in which steric configuration of three asymmetric points can be perfectly controlled, the reaction is performed by mild conditions and the chemical yield and the optical yield are extremely high. The optically active epoxides which can be efficiently produced by the production of the present invention are useful as stating materials of several kinds of compounds.

Optically active epoxides and a process for the production thereof

An optically active pentane compound of the general formula (I): ##STR1## wherein R.sub.1 represents a lower alkyl group having 1 to 4 carbon atoms, R.sub.2 represents a lower alkoxycarbonyl group having an alkoxy moiety of 1 to 4 carbon atoms, or a straight-chain or branched alkyl group having 1 to 7 carbon atoms which is unsubstituted or substituted with a hydroxy or protected hydroxy group, A represents a halogen atom, hydroxy, protected hydroxy, or ethynyl group, or a group of the formula ##STR2## B represents a hydrogen atom, hydroxy, protected hydroxy or acyloxy group, D represents a hydrogen atom, or A and B together can form an acetal or epoxy group, A and D together can form an ethylidene group, and B and D together can form a carbon-carbon direct bond, and the chiral central carbon atoms marked with symbols *, # and .thrfore. in said formula (I) alternatively have one of an R-configuration and an S-configuration Further, intermediates thereof, and a process for manufacturing the above compound are also disclosed

Optically active pentane derivatives and intermediates thereof, and

An optically active (S)- or (R)-chroman-2-ethanol compound of a general formula (I) ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, and a chiral central carbon atom marked with a symbol * in the formula (I) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (I) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (I) is easily synthesized from an easily available optically active starting material.

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Sendai, Japan

Seiichi Takano