Remote control of dieis-alder additions. Enantioselective synthesis of (2r). 1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

Article abstract of DOI:10.1016/S0957-4166(97)00433-3

The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan- 2'yl)-5,6-dimethylidene-7-oxabicyclo[2.2.1]hept-2-ene derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the prese