A highly stereoselective synthesis of 3-hydroxy-1-aryltetralin lignans based on the stereoselective hydroxylation of α,β-dibenzyl-γ-butyro-lactones: the first synthesis of (±)-cycloolivil

Abstract

Lignans of the 3-hydroxy-1-aryltetralin series 1 and 2 have been synthesised in good yields in a highly diastereoselective manner. The stereochemistry at C-1, C-2 and C-3 of 1 and 2 was completely controlled by an electrophilic addition of oxodiperoxymolybdenum(pyridine)hexamethylphosphoric triamide (MoOPH) to the metal enolates of α,β-disubstituted γ-butyrolactones 4 and the Friedel–Crafts type intramolecular cyclisation of 3. This method was applied to the stereoselective synthesis of (±)-cycloolivil 1e.