Total Synthesis of 6‑Deoxyerythronolide B via C–C Bond-Forming Transfer Hydrogenation

The 14-membered macro­lide 6-deoxy­erythro­nolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotyl­ation via transfer hydro­genation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythro­nolide reported, to date.