Radical-mediated synthesis of 3,4-dihydroisocoumarins: total synthesis of hydrangenol

Article abstract of DOI:10.1016/j.tetlet.2007.03.172

A radically promoted synthesis of 3,4-dihydroisocoumarins has been achieved in moderate to good yields using titanocene(III) chloride (Cp₂TiCl) as the radical initiator. The total synthesis of (±)-hydrangenol has been completed using this radical technology. Cp₂TiCl was prepared in situ from commercially available titanocene dichloride (Cp₂TiCl₂) and Zn-dust in THF under argon.