Yukio Mizuno

Isolation and structure elucidation of genuine oat phytoalexin, avenalumin I

Abstract The major phytoalexin from oat leaves has been identified as 2-[2-(4-hydroxyphenyDethenyl] -6-hydroxy-4H-3,1-benzoxazin-4-one ( A ).

Structures of new antibiotic substances, sakyomicin A, B, C, and D; X-ray crystal and molecular structure of sakyomicin A

The structure of a new antibiotic substance, sakyomicin A has been elucidated by X-ray crystallographic analysis and structures for its congeners, sakyomicin B, C, and D have been proposed from their spectroscopic properties.

Synthesis of sesquiterpenes, occidentalol, chamaecynone and related compounds characterised by a cis-eudesmane structure

In continuation of our synthetic work for constructing the cis-decalin skeleton by a double Michael annulation using 3-methyl-4-methylenecyclohex-2-enone and its congeners with dimethyl 3-oxoglutarate, the sesquiterpenes, occidentalol, chamaecynone, and related compounds have been synthesised in a stereoselective manner.

New stereoselective synthesis of 9-methyl-cis-decalin derivatives by double Michael reaction of 3-methyl-4-methylenecyclohex-2-enone and its congeners with dimethyl 3-oxoglutarate

Double Michael reaction of 3-methyl-, 2,3-dimethyl-, and 3,5-dimethyl-4-methylenecyclohex-2-enone with dimethyl 3-oxoglutarate in dimethyl sulphoxide in the presence of potassium fluoride gave stereoselectively 9-methyl-, 1,9-dimethyl-, and 4,9-dimethyl-6,8-dimethoxycarbonyl-cis-decahydronaphthalene-2,7-dione, respectively, and starting from these annulation products some sesquiterpenes having the cis-decahydronaphthalene skeleton were formally synthesised.

New stereoselective synthesis of 9-methyl-cis-decalin derivatives by double Michael reaction of 3,5-dimethyl-4-methylenecyclohex-2-enone and dimethyl 3-oxoglutarate; X-ray crystal and molecular structure of two of the products

Double Michael reaction of 3-methyl-, 2,3-dimethyl-, and 3,5-dimethyl-4-methylenecyclohex-2-enone with dimethyl 3-oxoglutarate in dimethyl sulphoxide in the presence of potassium fluoride as a catalyst gave stereoselectively 9-methyl-, 1,9-dimethyl-, and 4,9-dimethyl-6,8-dimethoxycarbonyl-2,7-dioxo-cis-decalin, respectively.