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Total synthesis of Hispidospermidine:
Reference: Frontier, A. J.; Raghavan, S.; Danishevsky, S. J. J. Am. Chem. Soc. 2000, 122, 6151. DOI
Keywords: Li/H → Li-Dithiane • Si-Alkynyl → H-Alkynyl • Alkyl-OH → Ketone-1,2-di • Ketone → Alkyl-OH • CompRed-Ketone/Ketone+B-H • O-H → O-SiEt3 • O-SiEt3 → O-H • Ether-5 • Jones oxidation • Alkyl-OH → Ketone-α-OR • Alkyl-OH → Ketone • Cu-Me+Enone • Enone+Ketone enolate • ConjAdd-Michael • CompE+-Enone/Alkyne+Cu-R • ConjAdd Cu-R • Li-Dithiane+Alkyl-X • Alkyl-X+Li-R • Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Reductive amination, B-H • N-H → N-Alkyl • Aldol-Na → Enone • Ketone → Ketone-α-OR • EnolSilane+MCPBA • Rubottom oxidation • ConjReduct Enone • ConjReduct-Silylation • Ketone-α-OH → Ketone-1,2-di • Ketone-1,2-di • Si-Vinyl → H-Vinyl • Enone → EnolSilane • Robinson annulation, Stork • Ketone enolate+Enone • Carbomercuration Alkyne • EnolSilane+Carbonium •
Reagents: BuLi(n) • Ceric ammonium nitrate • Hydroxide, sodium • LiCuMe2 • Methyl vinyl ketone • HCl • Li°/NH3 • SiEt3-OTf • Perbenzoic acid, 3-chloro • Fluoride, R4N+ • DMSO, (COCl)2 (Swern) • BH4-Na+ • SiEt3-OTf • MeMgI • HCl, H2O • CrO3, H2SO4 (Jones) • TsOH·Py • Alkyl-MgX • Cr2O7·2PyH (PDC) • BH3CN-Na+ • Hydroxide, potassium • LiN(SiMe3)2 • HgCl2 • SiMe3-Cl •

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