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Total synthesis of Galbulimima alkaloid GB 13:
Reference: Mander, L. M.; McLachlan, M. M. J. Am. Chem. Soc., 2003, 125, 2400. DOI
Keywords: Decarboxylation β-keto acid • Regitz diazo transfer • Claisen acylation, formate • Ketone enolate+Formate • Diazoketone • Photochemistry • CarboxAmide → Nitrile • Nitrile → Nitrile-α-SeR • Selenide → Selenoxide • O-SiMe2tBu → O-H • Birch reduction • EnolEther → Ketone • Alkyl-C≡N → Alkyl-H • Eschenmoser fragmentation • Ketone → EnolSilane • Wolff rearrangement • Cyclopentane • Selenoxide-Ei → EneNitrile • Epoxidation, peracid • Reductive amination, B-H • Amine-6 • N-OR → N-H • Saegusa oxidation • Ketone → Enone • Birch alkylation • CarboxAcid enolate+Alkyl-X • Alkyl-X+Enolate • Friedel-Crafts Alkylation • Cyclohexane • Bicyclo(331) • Diels-Alder, EneNitrile • Ketone → Oxime • O-H → O-MOM • Ketone → EnolSilane • O-MOM → O-H • Alkyl-OH → Ketone • N-C(O)R → N-H • O-MOM → O-H • Alkyl-OH → Ketone-α-OR • Enone → Allyl-OH • Ketone → Alkyl-OH • CompRed-Ketone/Nitrile+M-H • O-H → O-MOM • N-H → N-C(O)R •
Reagents: Acetic acid • Chloromethyl ether • DMAP • Formate, ethyl • NEt3 • Photochemistry • NH(SiMe3)2 (HMDS) • Acetyl chloride, trichoro • NEt3 • KN(SiMe3)2 • Diselenide, phenyl • H2O2 • Fluoride, R4N+ • AlH4-Li+ • Chloromethyl ether • DMAP • NEtiPr2 • Li°/NH3 • HCl, MeOH • AlH4-Li+ • Perbenzoic acid, 3-chloro • Dess-Martin • Hydrazine, p-nitrophenylsulfonyl • Pyridine • NH2OH • Pyridine • ZrCl4 • BH4-Na+ • Zn° • Acetic anhydride • Acetic anhydride, trifluoro • LiNiPr2 • SiMe3-Cl • Pd(OAc)2 • HCl, H2O • Dess-Martin • HCl, H2O • Carbonate, potassium • DMSO (solvent) • Li°/NH3 • H2SO4 • Acetone (solvent) • Butadiene, 2-OR • Yb(thd)3

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