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Total synthesis of Gelsemine:
Reference: Ataraschi, S.; Choi, J-K.; Ha, D-C.; Hart, D.J.; Kuzmich, D.; Lee, C-S.; Ramesh, S.; Wu, S.C. J. Am. Chem. Soc., 1997, 119, 6226-6241 DOI
Keywords: Diels-Alder, Maleic anhydride • Ketone → Ketal • O-THP → O-H • Ozonolysis • Mg-Aryl+Carboxester • CarboxEster+Mg-R • O-H → O-Me • N-H → N-C(O)R • Ozonolysis • O-Bn → O-H • Alkyl-OH → Aldehyde • Wittig-ketomethyl → Enone • Ketone → EnolSilane • Selenoxide-Ei → Ene • Mitsunobu → SeR • CarboxImide+BH • CarboxAmide enolate+Alkyl-X • Alkyl-X+Enolate • Wittig-carboxymethyl → EnoateEster • Ketone enolate+Isocyanate • Radical cyclization(Aryl) • Acetal → Ether • Petasis reagent • Radical cyclization(Alkyl) •
Reagents: PPh3 • LiNiPr2 • SiMe3-Cl • TsOH • Selenocyanate, o-nitrophenyl • PBu3 • H2O2 • BH4-Na+ • NaH • LiNiPr2 • Chloromethyl ether • O3 • Formate, ethyl • Thiol, phenyl • TsOH • PhMgBr • MeI • DMSO (solvent) • KH • TsOH • Acetic anhydride • DMAP • HSnBu3 • TsOH • O3 • HCl, H2O • HSiEt3 • Acetic acid, trifluoro • AIBN • B(Br)3 • Dess-Martin • TiCp2Me2 • HSnBu3 • AIBN •

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