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Total synthesis of Aspidophylline A:
Reference: Zu,L.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 8877–8179. DOI
Keywords: Ketone → Ketal(Me) • N-Bn → N-H • N-H → N-SO2R • Ketal → Ketone • Ketone → Alkyl-OH • Alkyl-OH → Ketone-α-NR2 • N-SO2R → N-H • Fischer indole • Diels-Alder, Maleic anhydride • Decarboxylation Oxidative • N-H → N-SO2R • Pd-Heck coupling • Enone → Ketone • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Alkene cleavage • Lactone-6 • Lactone → Ester • Ether-5 • Ketone → Hydrazone • Amine-6 •
Reagents: Orthoformate • TsOH • Na°/NH3 • BuLi(n) • Carbonate, potassium • Pd(PPh3)4 • Piperidine, pentamethyl • FeCl3 • In° • LiN(SiMe3)2 • Allyl-I • DMPU (solvent) • BH4-Na+ • OsO4, NaIO4 • BH4-Na+ • H2SO4 • Dess-Martin • Hydrazine, phenyl • Carbonate, potassium • Mg° • Formic acid •

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