Chisso Corporation

Asahi Denka Kogyo K.k.

Asahi Denka Kogyo Kabushiki Kaisha

Other

Adeka Argus Chemical Co., Ltd.

Kunio Ogasawara

Seiichi Takano

Naoyuki Yoshida

Toshihiro Shibata

Norio Kurosawa

Takahiko Taniguchi

Masaki Kimura

Tetsuya Ogawa

Yohichi Shimazaki

Yoshinori Sekiguchi

Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-[(dimethylmethylene)dioxy]-5-hydroxy-tricyclo[5.2.1.0]dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo[5.2.1.0]deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.

Intermediates and improved processes for the preparation of neplanocin A

Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-[(dimethylmethylene)dioxy]-5-hydroxy-tricyclo[5.2.1.0dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo[5.2.1.0]deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.

Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-&lsqb;(dimethylmethylene)dioxy&rsqb;-5-hydroxy-tricyclo&lsqb;5.2.1.0 &rsqb;dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo&lsqb;5.2.1.0 &rsqb;deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.

Process for the preparation of optically active enones and intermediates thereof

Method of catalytically removing a protective group containing an allyl group using a reducing agent

By treating the reactant of 3,4-ditrimethylsilyloxytricyclo&lsqb;4.2.1.0,&rsqb;nona-3,7-diene and binaphthol monoether-tin tetrachloride complex, optically active acyloin is produced. Using the optically active acyloin compound as a starting material, optically active oxydicyclopentadiene useful as several kinds of intermediates can be obtained efficiently.

Method for producing an optically active acyloin

Intermediate compounds, including 2-(t-butyldimethylsilyloxymethyl)-3,4-&lsqb;(dimethylmethylene)dioxy&rsqb;-5-hydroxy-tricyclo&lsqb;5.2.1.0,&rsqb;dec-8-ene, which are useful for the synthesis of neplanocin A having strong antitumor activity. Improved processes for the preparation of neplanocin A, starting from optically active 2-hydroxymethyl-5-hydroxy-tricyclo&lsqb;5.2.1.0,&rsqb;deca-3,8-diene and via a key step comprising a retro-Diels-Alder reaction of the above intermediate.

Optically active oxodicyclopentadiene is produced by adding lipase into ketoalcohol (1) and vinyl acetate, stirring them to obtain optically active acetate, and methylating and oxidizing to cleavage the reactant, and treating the product under basic conditions. ##STR1##

Method for producing oxodicyclopentadiene

The invention relates to the preparation of (1S,2R)-cis-1-aminoindan-2-ol represented by formula (IX): ##STR1## and intermediates derived therein.

Process for preparation of indenol

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.

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Sendai, Japan

Kunio Ogasawara