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1′-Epi-stegobinone [(2S,3R,1′S)-2,3-dihydro-2,3,5-trimethyl-6-(1′-methyl-2′-oxobutyl)-4H-pyran-4-one], an inhibitor of stegobinone, which is the sex pheromone of drugstore beetle (Stegobium paniceum L.), was synthesized by stereocontrol at C-2 and C-1′ starting from ethyl (R)-3-hydroxybutanoate and methyl (R)-3-hydroxypentanoate.

(1991). A New Synthesis of 5-Aminolevulinic Acid. Agricultural and Biological Chemistry: Vol. 55, No. 6, pp. 1687-1688.

(1991). Synthesis of Both Enantiomers of 4-Hexanolide and 4-Dodecanolide. Agricultural and Biological Chemistry: Vol. 55, No. 6, pp. 1685-1686.

(2S, 3R, 1'S, 2'S)-Serricorole (1) and (2S, 3R, 1'R)-serricorone (2), sex pheromone components of the cigarette beetle (Lasioderma serricorne F.), were synthesized, starting from the enantiomers of methyl 3-hydroxypentanoate. The stereochemistry of the naturally occurring 1 was determined to be 2S, 3R, 1'S, 2'S, and that of 2 to be 2S, 3R, 1'RS by comparing between the CD spectra of the natural and synthetic samples.

A 1:1 mixture of (Z, Z)-3,13-octadecadien-1-ol and its (E, Z)-isomer was synthesized by a Wittig reaction whose stereoselectivity was adjusted to give the products in the required ratio. The corresponding acetate mixture is useful as the attractant for Synanthedon hector.

(2S,3R,1′S,2′S)-Serricorole (1) and (2S,3R,1′R)-serricorone (2), sex pheromone components of the cigarette beetle (Lasioderma serricorne F.), were synthesized, starting from the enantiomers of methyl 3-hydroxypentanoate. The stereochemistry of the naturally occurring 1 was determined to be 2S,3R,1′S,2′S, and that of 2 to be 2S,3R,1′RS by comparing between the CD spectra of the natural and synthetic samples.

Both the enantiomers of (Z)-cis-9,10-epoxy-6-heneicosene (2), a pheromone component of Phragmatobia fuliginosa L, were synthesized by employing the Sharpless asymmetric epoxidation as the key step.