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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 (Part 1)
Keywords: Ketone → EnolSilane • N-H → N-MOM • EnolEther → Ketone • Ketone → Alkyl-OH • O-H → O-Ethoxyethyl • N-C(O)R → N-H • N-MOM → N-H • Lactone-6 • Ketone → Ketone-α-OR • Ketone → EnolTriflate • Pd-Carboxylation • EnolTriflate → 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 • PdCl2(dppf) • NBu3 • AlMe3 • NaH • HCl, H2O • DBU • Vinyl-OR • TsOH·Py • Cyanide, sodium • DMSO (solvent) • MeOTf • Cyanide, sodium • DMSO (solvent) • HCl, H2O • NEtiPr2 • AlHiBu2 • TsOH·Py • Pyridine, 2,6-di-tBu • Pd2(dba)3 • Ag3PO4 • NEt3

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