Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant

Article abstract of DOI:10.1016/S0040-4020(98)00918-1

Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TRAP and NMO. Subsequent Wittig reaction afforded 2-alk- 1-enyltetrahydrofurans (2 and 3) that can be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E,6E)- nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit fly, Anastrepha suspensa.