image

Total synthesis of Coriolin:
Reference: Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1981, 103, 7380. DOI
Keywords: Ketone -> Ketal • Cyclopropane Hydrogenolysis • Dehydration -> Ene • Epoxidation, peracid • Ketal -> Ketone • Dehydrosulfonylation -> Enone • Epoxidation, peracid • Ketone -> Enolsilane • Epoxide reduction • O-H -> O-SiMe3 • Mannich • Imonium+Enolate • O-SiMe3 -> O-H • ConjAdd M-SR • Ketone -> Ketone-α-SR • Simmons-Smith • Dienone -> Enone • Epoxide -> Allyl-OH • Hofmann elim -> Enone • Si-Allyl+Ketone • Ketone+Si-R • Sakurai allylation • Sulfide -> Sulfone • Ketone enolate+Alkyl-X •
Reagents: NEt3 • Glycol • Camphor sulfonic acid • Disulfide, methyl • KH • CH2I2, ZnEt2 • H2, Pt • SOCl2 • Perbenzoic acid, 3-chloro • HClO4 • DBU • Li°/NH3 • Perbenzoic acid, 3-chloro • DBU • LiNiPr2, HMPA • SiMe3-Cl • Na°/Naphth • CH2=NMe2+I- • HF·Py • MeI • DBU • Fluoride, Bu4N+ • Allyl-SiR3 • KH • Perbenzoic acid, 3-chloro • Allyl-SiR3 • Allyl-SiR3

Syntheses Home