A NOVEL BASE-PROMOTED REARRANGEMENT OF EUDESMANOLIDE SESQUITERPENOID TO THE SALVIALANE SESQUITERPENE

An eudesmanolide sesquiterpene epoxide has been transformed to an α-hydroxy ketone with the salviane sesquiterpene skeleton through a novel carbon-carbon rearrangement promoted by excess of NaOMe in Et2O at room temperature which accomplished the first synthesis of the salviane kind of sesquiterpene skeleton. A possible reaction mechanism is also discussed.