image

Total synthesis of Cycloepoxydon:
Reference: Li, C.; Pace, E. A.; Liang, M.-C.; Lobkovsky, E.; Gilmore, T. D. Porco, J. A. J. Am Chem. Soc. 2001, 123, 11308. DOI
Keywords: Ketone -> Ketal --- Pd/Sn-Vinyl+Vinyl-X --- Stille coupling --- Enone -> Allyl-OH --- O-SiPh2tBu -> O-H --- Ketal -> Ketone --- Epoxidation, nucleophilic(asym) Enone --- Epoxide -> Diol --- Phenol -> Quinone --- Epoxidation, peracid
Reagents: Iodosobenzene-OAc --- Hydroperoxide, trityl --- DEET --- Vinyl-SnR3 --- Pd2(dba)3 --- AlHiBu2 --- Perbenzoic acid, 3-chloro --- HF --- Acetonitrile (solvent) --- HF --- Acetonitrile (solvent)

Syntheses Home