Yutaka Nakazono

Synthesis of both the enantiomers of dihydroactinidiolide, a pheromone component of the red imported fire ant

Abstract Both the enantiomers of dihydroactinidiolide (4,4,7a-trimethyl-2-oxo-2, 4,5,6,7,7a-hexahydrobenzofuran) were synthesized in 15 steps from ( S )-3-hydroxy- 2,2-dimethylcyclohexanone.

Lipase-catalyzed kinetic resolution of methyl 4-hydroxy-5-tetradecynoate and its application to a facile synthesis of japanese beetle pheromone

Abstract A kinetic resolution of methyl 4-hydroxy-5-tetradecynoate is accomplished by a lipase-catalyzed enantioselective acylation in organic solvent. Acylation of methyl 4-hydroxy-5-tetradecynoate with succinic anhydride in an organic solvent yields methyl (R)-4-succinoyloxy-5-tetradecynoate with over 90% e.e.. Furthermore, this optically active diester was converted to (R)-5-(1-decynyl)oxacyclopentan-2-one by lipase-catalyzed enantioselective lactonization which enhanced its e.e. over 99%. The Japanese beetle pheromone (R,Z)-(-)-5-(1-decenyl)oxacyclopentan-2-one is synthesized in one step from this optically active lactone.

Lipase-catalyzed kinetic resolution of 2,3-epoxy-8-methyl-1-nonanol, the key intermediate in the synthesis of the gypsy moth pheromone

Abstract Lipase-catalyzed enantioselective acylation of (±)-2,3-epoxy-8-methyl-1-nonanol with acetic anhydride in diisopropyl ether yielded (2S, 3R)-1-acetoxy-2,3-epoxy-8-methylnonane with 79% enantiomeric excess (ee). The optical purity of the epoxy ester was improved up to 95% ee by a second step of lipase-catalyzed enantioselective alcoholysis in diisopropyl ether.

Synthesis of the Enantiomers of (Z)-5(1-Octenyl)oxacyclopentan-2-one, a Sex Pheromone of the Cupreous Chafer Beetle, Anomala cuprea Hope

Synthesis of the Enantiomers of (Z)-5-(1Octenyl)oxacyclopentan-2-one, a Sex Pheromone of the Cupreous Chafer Beetle, Anomala cuprea Hope Eiichiro Fukusaki, Shuji Senda, Yutaka Nakazono & Tetsuo Omata To cite this article: Eiichiro Fukusaki, Shuji Senda, Yutaka Nakazono & Tetsuo Omata (1992) Synthesis of the Enantiomers of (Z)-5-(1-Octenyl)oxacyclopentan-2-one, a Sex Pheromone of the Cupreous Chafer Beetle, Anomala cuprea Hope, Bioscience, Biotechnology, and Biochemistry, 56:7, 1160-1161, DOI: 10.1271/bbb.56.1160 To link to this article: http://dx.doi.org/10.1271/bbb.56.1160

Large-scale preparation of (+)-disparlure, the gypsy moth pheromone, by a practical chemico-enzymatic procedure

Abstract The Sharpless asymmetric epoxidation of 8-methyl-2-nonen-1-ol performed on a large scale (over 5 moles) at room temperature gave (2S, 3R)-2, 3-epoxy-8-methyl-1-nonanol with 52%ee. The produced epoxy alcohol of low optical purity was subjected to lipase-catalyzed enatioselective acylation in order to increase the optical purity up to 85%ee. Recrystalyzation of the corresponding 3, 5-dinitrobenzoate gave optically pure epoxy alcohol. (+)-Disparlure, the gypsy moth pheromone, was synthesized in two steps from the thus obtained optically pure epoxy alcohol.

Preparation of carboxyalkyl acrylate by lipase-catalyzed regioselective hydrolysis of corresponding methyl ester

Abstract Carboxyalkyl acrylate was synthesized by lipase-catalyzed regioselective hydrolysis of corresponding methyl ester, methoxycarbonylalkyl acrylate, which was conveniently prepared from vinyl acrylate and hydroxyalkanoic acid methyl ester by lipase-catalyzed transesterification in an organic solvent.