Science. 1977 Aug 19;197(4305):789-92. doi: 10.1126/science.197.4305.789.
(Z)-5-(1-Decenyl)dihydro-2(3H)-furanone, isolated from virgin female Japanese beetles (Popillia japonica) attracted males of the species infield bioassays. However, the synthesized racemic mixture of this compound did not attract male Japanese beetles. The Z and E isomers and the saturated analog of both enantiomers of this compound were synthesized stereospecifically. Pure synthetic (R,Z)-5-(1-decenyl)dihydro-2(3H)-furanone was competitive with live females and with the pheromone isolated from live females in attracting males. Male response was strongly inhibited by small amounts of the S,Z isomer. Although the E isomer and the saturated analog of the pheromone are present in the material obtained from females, the role of these compounds in mediating the insect's behavior is unclear.
（Z）-5-（1-癸烯基）二氢-2（3H）-呋喃酮，从处女雌性日本甲虫（Popillia japonica）中分离出来，在田间生物测定中吸引同种雄性。然而，该化合物的合成外消旋混合物并没有吸引雄性日本甲虫。该化合物的 Z 和 E 异构体以及两种对映体的饱和类似物均被立体特异性合成。纯合成（R，Z）-5-（1-癸烯基）二氢-2（3H）-呋喃酮与活体雌性和从活体雌性中分离出的信息素在吸引雄性方面具有竞争性。雄性反应受到少量 S，Z 异构体的强烈抑制。尽管 E 异构体和信息素的饱和类似物存在于从雌性获得的物质中，但这些化合物在介导昆虫行为中的作用尚不清楚。
