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Total synthesis of Coriolin:
Reference: Trost, B. M.; Curran, D. P. J. Am. Chem. Soc. 1981, 103, 7380. DOI
Keywords: O-H → O-SiMe3 • O-SiMe3 → O-H • ConjAdd M-SR • Ketone → Ketone-α-SR • Simmons-Smith • Cyclopropane • Dienone → Enone • Epoxide → Allyl-OH • Hofmann elim → Enone • Si-Allyl+Ketone • Ketone+Si-R • Cyclopentane • Sulfide → Sulfone • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Mannich • EnolSilane+Iminium • Iminium+Enolate • Cyclopropane Hydrogenolysis • Dehydration → Ene • Epoxidation, peracid • Ketal → Ketone • Dehydrosulfonylation → Enone • Epoxide reduction • Epoxidation, peracid • Enone → EnolSilane • Ketone → Ketal • CompE+-Ketone/Ketone+glycol •
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 • Acetamide, bistrimethylsilyl • CH2=NMe2+I- • HF·Py • MeI • DBU • Fluoride, R4N+ • Allyl-SiR3 • Allyl-I • KH • Perbenzoic acid, 3-chloro • Allyl-SiR3 • Allyl-SiR3 • HMPA (solvent) •

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