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Total synthesis of Gelsemine (Part 2):
Reference: Madin, A.; Meier, J. P.; O'Donnell, C. J.; Oh, T.; Old, D. W.; Overman, L. E.; Sharp, M. J. J. Am. Chem. Soc. 2005, 1127, 18046. DOI
Keywords: Ketone -> Enolsilane • N-H -> N-MOM • Enolether -> Ketone • Ketone -> Alkyl-OH • O-H -> O-Ethoxyethyl • N-MOM -> N-H • Lactone-6 • Ketone -> Ketone-α-OR • Ketone -> Vinyl-OTf • Pd-Carboxylation • Vinyl-OTf -> EnoateEster • CarboxEster -> Carboxamide • Aziridine • Aziridine+Cyanide • O-Ethoxyethyl -> O-H • Lactone -> Lactol • Lactol -> Ether • Pd-Heck coupling • Lactam-5 •
Reagents: KN(SiMe3)2 • SiEt3-Cl • Iodosobenzene • BF3·OEt2 • KN(SiMe3)2 • Tf2N-2-Py-5-Cl • CO • NBu3 • AlMe3 • NaH • HCl • DBU • Vinyl-OR • TsOH·Py • Cyanide, sodium • DMSO (solvent) • MeOTf • Cyanide, sodium • DMSO (solvent) • HCl • NEtiPr2 • TsOH·Py • Pyridine, 2,6-di-tBu • Pd2(dba)3 • Ag3PO4 • NEt3

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