Kao Soap Company, Ltd.

Hiroshi Ikeda

Yoshiaki Inamoto

Yoshiaki Fujikura

Naotake Takaishi

Koji Aigami

Motoyoshi Ohsugi

Kiyoshi Tsuchihashi

Yoshiaka Inamoto

Yoshiaka Fujikura

1-Halogenotricyclo [4.3.1.1.sup.2,5 ] undecanes are prepared by reacting tricyclo [4.3.1.1.sup.2,5 ] undecane with bromine or by reacting tricyclo [4.3.1.1.sup.2,5 ] undecane-1-ol with thionyl halide. The compounds are useful intermediates for preparing 1-aminotricyclo [4.3.1.1.sup.2,5 ] undecane hydrochloride which has antiviral activity.

1-Halogenotricyclo [4.3.1.1.sup.2,5 ] undecane and process for the

1-Acetylaminotricyclo [4.3.1.1.sup.2,5 ] undecane is prepared by reacting either (a) 1-substituted tricyclo [4.3.1.1.sup.2,5 ] undecane, wherein the substituent is Cl, Br or OH, or (b) endo-2-hydroxymethyl-exo-2,3-trimethylenenorbornane with acetonitrile, in the presence of sulfuric acid. 1-Acetylaminotricyclo [4.3.1.1.sup.2,5 ] undecane is useful as an intermediate to prepare antiviral substances.

1-Acetylaminotricyclo [4.3.1.1.sup.2,5 ] undecane and process for the

1-Amino-tricyclo [4.3.1.1.sup.2,5 ] undecane is prepared by alkaline hydrolysis of 1-acetylamino-tricyclo [4.3.1.1.sup.2,5 ] undecane, and its acid addition salts are prepared by neutralizing it with an acid. The compounds possess antiviral activity.

1-Aminotricyclo (4.3.1.1.sup.2,5) undecane and salts thereof

This invention relates to novel 3-amino-4-homoisotwistane (3-amino-tricyclo [5.3.1.0.sup.3,8 ] undecane), an acid addition salt thereof, and to a process for producing the same.

3-Amino-4-homoisotwistane and an acid addition salt thereof and a

8-EXO-HYDROXYMETHYL-ENDO-TRICYCLO [5.2.1.0.sup.2,6 ] DECANE IS PREPARED BY HYDROGENATING 8- AND 9-EXO-FORMYL-ENDO-TRICYCLO [5.2.1.0.sup.2,6 ] DECA-3-ENES.

8-Exo-hydroxymethyl-endo-tricyclo [5.2.1.0.sup.2,6 ]decane

3-Aminomethyl-4-homoisotwistane acid addition salts produced by the steps of reducing 4-homoisotwistane-3-carboxylic acid amide or 4-homoisotwistyl-3-cyanide represented by the following general formula, and converting 3-aminomethyl-4-homoisotwistane into its addition salt- ##STR1## wherein R stands for the group of the formula --CONH.sub.2 or --CN.

3-Aminomethyl-4-homoisotwistane and its salt and process for producing

4-HOMOISOTWISTANE-3-CARBOXYLIC ACID ESTERS HAVE BEEN PREPARED AND SHOWN TO POSSESS SUPERIOR ANTIVIRAL EFFECTS.

4-Homoisotwistane-3-carboxylic acid esters and a process for producing

Tricyclo[5.3.1.0.sup.3,8 ]undec-2-ene is novel and prepared by reacting 3-halogeno-4-homoisotwistane with a dehydrohalogenating agent.

Tricycli Bredt Compound, Tricyclo[5.3.1.0.sup.3,8 ]Undec-2-ene

The compound 4-exo-hydroxy-endo-tricyclo[5.2.2.0.sup.2,6 ]-undec-8-ene having the formula (I): ##STR1## is prepared by subjecting endo-tricyclo[5.2.2.0.sup.2,6 ]undeca-3,8-diene having the formula (II): ##STR2## to oxymercuration and reduction with sodium borohydride.

4-Exo-hydroxy-endo-tricyclo [5.2.2.0.sup.2,6 ]undec-8-ene

4-HOMOISOTWISTYL BROMIDE HAS BIOLOGICAL ACTIVITIES TO PLANTS. It is useful as an intermediate to produce 3-acetylamino-4-homoisotwistane which has an antiviral effect and a biological activity to plants. 4-homoisotwistyl bromide is obtained by reacting 4-homoisotwistane with liquid bromine.

4-Homoisotwistyl bromide

4-HOMOISOTWIST-3-YL-CARBINOL HAVING THE FORMULA (II): ##STR1## is prepared by reducing 4-homoisotwistane-3-carboxylic acid or a salt or lower alkyl ester thereof, having the formula (I): ##STR2## wherein A is hydrogen, one equivalent of an alkali metal or an alkaline earth metal, or an alkyl group having 1 to 8 carbon atoms.

4-Homoisotwist-3-yl-carbinol

4-HOMOISOTWISTANE-CARBOXYLIC ACID IS PREPARED BY REACTING 4-HOMOISOTWISTANE WITH T-BUTYL ALCOHOL AND FORMIC ACID OR CARBON MONOXIDE, IN THE PRESENCE OF SULFURIC ACID AS CATALYST.

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Wakayama, Japan

Hiroshi Ikeda