A Total Synthesis of Dehydrojuvabione

Dehydrojuvabione의 전합성

A total synthesis of dehydrojuvabione which has high juvenile hormone activity, is described. The kinetic enloate of mesityl oxide is used as nucleophilic synthon for this synthesis. 1,4-Dioxaspiro [4,5] decan-8-carboxaldehyde was treated with kinetic enolate of mesityl oxide to give 8-(1'-hydroxy-5'-methyl-3'-oxo-4'-hexenyl)-1,4-dioxaspiro [4,5] decane. The latter compound was dehydrated. The resulted dienone was treated with lithium dimethylcuprate. After that, appropriate transformation was performed to give dehydrojuvabione.