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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 • Bicyclo(222) • Birch reduction • CarboxEster → CarboxAcid • CompE+-CarboxEster/O-Si+KOH • C-CO2H → C-N • N-C(O)OR → N-H • O-SiEt3 → O-H • N-H → N-C(O)OR • Ketone → EnolSilane • Wittig-methyl → Diene • CompE+-Aldehyde/CarboxEster+Wittig • Aza-Claisen • Amine-6 • EnAmine → EnAmine-β-Br • CompNu-Enamide/Alkene+Br2 • Mannich • Amine-5 • Curtius • C-CO2H → C-N • Allylic oxidation → Enal • CyanoAmine • N-H → N-Alkyl • EnolCarbonate → Ketone • CompE+-Carbonate/Carbamate+KOH •
Reagents: LiNiPr2 • SiiPr3-OTf • Acrylate • AlCl3 • SeO2 • PPh3=CH2 • Hydroxide, potassium • Azide, diphenylphosphoryl • Acetic acid, trifluoro • Formaldehyde • Fluoride, R4N+ • KH • 18-crown-6 • O=C(OR)Cl • Hydroxide, potassium • Bromine • Piperidine, pentamethyl • Acetic acid, trifluoro •

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