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Total synthesis of Coriolin:
Reference: Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1981, 103, 7380. DOI
Keywords: Si-Allyl+Ketone • Sakurai allylation • Ketone -> Ketal • Sulfide -> Sulfone • Cyclopropane Hydrogenolysis • Dehydration -> Ene • Epoxidation, peracid • Ketal -> Ketone • Dehydrosulfonylation -> Enone • Epoxidation, peracid • Ketone -> Enolsilane • Epoxide reduction • O-H -> O-SiMe3 • Mannich • O-SiMe3 -> O-H • ConjAdd M-SR • Ketone -> Ketone-α-SR • Ketone enolate+Allyl-X • Simmons-Smith • Dienone -> Enone • Epoxide -> Allyl-OH • Hoffmann elim -> Enone •
Reagents: Allyl-SiR3 • Fluoride, Bu4N+ • NEt3 • Glycol • Camphor sulfonic acid • Disulfide, methyl • KH • Allyl-SiR3 • Allyl-SiR3 • KH • Perbenzoic acid, 3-chloro • 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 •

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