Glycosylation of an allenic erythronolide.

A concise route to a glycosylated allenic erythronolide was achieved. Key findings include the preparation of a desosamine sulfoxide donor and the use of the donor to glycosylate bulky acceptors. Additionally, the new reagent was used to prepare allene-containing macrocycles and to realize a four-step synthesis of macrolide 6 from bis[allene] 5. The longest linear sequence required to prepare 6 from commercial reagents was 15 steps.