A Common Synthetic Protocol for the Cyclic and Acyclic Core of Migrastatin, Isomigrastatin, and Dorrigocin via a Chiral β-Hydroxy-γ-butyrolactone Intermediate

A facile synthetic route has been developed for the synthesis of the cyclic and acyclic cores of migrastatin, isomigrastatin, and dorrigocin. The common synthetic route goes via a β‐hydroxy‐γ‐butyrolactone intermediate that is obtained by a PdII‐catalysed asymmetric allylic intramolecular cyclization of 3‐hydroxy‐2‐methylhex‐5‐enoic acid following a protocol developed by White and coworkers. The synthesis of a key intermediate chiral β‐hydroxy‐γ‐butyrolactone (A) by PdII‐catalysed stereoselective allylic C–H oxidation is reported. A common synthetic route to transform this intermediate into key building blocks for the synthesis of migrastatin family members has been developed.