Synthesis of the nogalamine fragment 4 began with Noyori asymmetric reduction of achiral 37 to give 38, followed by oxidative ring expansion via an Achmatowicz reaction to yield dihydropyranone 39 (Scheme 4C). Tang's chiral catalyst-directed acylation and Pd-catalyzed glycosidation strategies afforded intermediate 41 as an 8:1 mixture of α:β anomers. Luche reduction, epoxidation and ring-opening with HNMe2 afforded 43 in 16% yield over the three-step sequence. A final debenzylation is all that is required for the nogalamine sugar 4, but at this stage, the alcohol was left protected as the benzyl ether.