Enantioselective Synthesis of the ent-Lomaiviticin A Bicyclic Core

The bicyclic core of ent-lomaiviticin A was prepared in 11 operations from (S)-1-phenyl-2-propyn-1-ol in a two-directional route that features (1) a double Ireland Claisen rearrangement and (2) a double olefin metathesis reaction to form the key C–C bonds of the target.