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Total synthesis of Gelsemine (Part 1):
Reference: Earley, W. G.; Jacobsen, J. E.; 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 2)
Keywords: Diels-Alder, EnoateEster • Birch reduction • Allylic oxidation → Enal • CarboxEster → CarboxAcid • C-CO2H → C-N • N-C(O)OR → N-H • N-H → N-Alkyl • O-SiEt3 → O-H • N-H → N-C(O)OR • EnolCarbonate → Ketone • Ketone → EnolSilane • Wittig-methyl • Aza-Claisen • Amine-6 • Enamine → Enamine-β-Br • Mannich • Curtius • C-CO2H → C-N •
Reagents: LiNiPr2 • SiiPr3-OTf • Acrylate • AlCl3 • SeO2 • PPh3=CH2 • Hydroxide, potassium • Azide, diphenylphosphoryl • Acetic acid, trifluoro • Formaldehyde • Fluoride, R4N+ • KH • 18-cr-6 • O=C(OR)Cl • Hydroxide, potassium • Bromine • Piperidine, pentamethyl • Acetic acid, trifluoro •

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