Iterative Benzyne−Furan Cycloaddition Reactions: Studies toward the Total Synthesis of <i>e</i><i>nt-</i>Sch 47554 and <i>e</i><i>nt-</i>Sch 47555

7-Fluoro-5,8-dimethoxy-1-naphthol, prepared from the lithiation and benzyne formation from 1,4-difluoro-2,5-dimethoxybenzene and Diels−Alder cycloaddition with furan, was sequentially C-glycosidated under Suzuki conditions and O-glycosidated using di-O-acetyl-l-rhamnal to provide the corresponding β-naphthyl C,O-disaccharide. Further lithiation, benzyne formation, and cycloaddition with furan gave an oxa-bridged 1,4-dihydroanthracenyl C,O-disaccharide, a model compound relevant to the total synthesis of Sch 47555.