The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.
- Epoxide ring opening
- Fusarisetin A
- Oxidative lactonization
- Yamamoto asymmetric epoxidation