Kuraray Co., Ltd.

Chisso Corporation

Nippon Kayaku Kabushiki Kaisha

Chikara Kaneko

Nobuya Katagiri

Yoshin Tamai

Koichi Kanehira

Masahiro Torihara

Junko Sato

Masayuki Sato

Hiromichi Ogasawara

Cyclopentenecarboxamide derivative, method for preparing the same and bicycloamide derivative used therein

Cyclopentenecarboxamide derivative, method for preparing the same bicycloamide derivative used therein

A cyclopentenecarboxamide derivative represented by the formula (I): ##STR1## and a method for preparing the cyclopentencarboxamide derivative. A bicycloamide derivative represented by the formula (II): ##STR2## and a method for preparing the bicycloamide derivative.

Cyclopentenecarboxamide derivative, method for preparing the same and

There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Provided are optically active 5,6-epoxyhexanoic acid esters and novel optically active 6-substituted tetrahydropyran-2-one derivatives. That is, optically active 6-chloromethyltetrahydropyran-2-one can be synthesized by lactonizing optically active 2,2-dimethyl-6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-one to form optically active 6-chloromethyltetrahydropyran-2,4-dione; reacting the thus formed compound with hydrogen in the presence of a catalyst to obtain optically active 6-chloromethyl-4-hydroxytetrahydropyran-2-one; subjecting this compound to a dehydration reaction, thereby obtaining optically active 6-chloromethyldihydropyran-2-one; reacting this compound with hydrogen in the presence of a catalyst to form optically active 6-chloromethyltetrahydropyran-2-one; and then treating this compound under basic conditions to prepare an optically active 5,6-epoxyhexanoic acid ester represented by the formula (6) ##STR1## (wherein the symbol * represents an asymmetric carbon atom, and R is a methyl group or an ethyl group).

Optically active 2,2-dimethyl-1,3-dioxin-4-ones and method for preparing

There are provided novel and optically active 2,2-dimethyl-1,3-dioxin-4-ones which are useful as starting materials for physiologically active compounds, functional materials or the like. Furthermore, a method for preparing an optically active compound comprises reacting a racemic 1,3-dioxin-4-one with vinylacetate in the presence of lipase to resolve the racemic compound into optically active compound represented by the formula (3) ##STR1## and an optically active compound represented by the formula (4) ##STR2## which is an antipode of the compound represented by the formula (3).

The present invention relates to a process for producing cyclobutane derivatives represented by general formula (28): ##STR1## (wherein R represents a substituent; R.sub.2 represents an electron attracting group and Nu represents a substituent corresponding to nucleophilic reagent), by reacting a compound represented by general formula (27): ##STR2## (wherein R has the same significance as defined above and R.sub.1 represents an electron attracting group) with nucleophilic reagents Nu.sup..crclbar. in a solvent. The compounds of formula (28) are useful as intermediates for synthesis of, for example, 9-[2,3-bis(hydroxymethyl)cyclobutan-1-yl]guanine which is expected to be useful as an antiviral agent.

Process for producing cyclobutane derivative

A process for producing 3-oxo-6-formyl-2-oxabicyclo[3.3.0]-6-octene useful as an intermediate for producing prostaglandins, via a few steps from raw materials which can be relatively easily prepared. The process comprises subjecting 2,2-dimethyl-1,3-dioxin-4-one and cis-2-cyclopenten-1,4-diol to addition reaction in a solvent, preferably under a photo-irradiation, removing the solvent from the reaction mixture, adding water to the resulting adducts and reacting the resulting mixture on heating.

Process for producing an aldehydelactone

A process for producing 1,3-dioxin-4-one derivatives having a lower alkyl group at 2-position and useful as a starting raw material for prostaglandins, with a high yield is provided, which process comprises reacting formyl Meldrum's acid with a lower aliphatic carbonyl compound of 2 to 4 carbon atoms in a solvent containing the carbonyl compound at 100.degree. to 120.degree. C., while portionwise adding the acid into the solvent, the total quantity of the acid added being 0.2 mol or less per liter of the solvent.

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Sendai, Japan

Chikara Kaneko