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Total synthesis of Histrionicotoxin:
Reference: Stork, G.; Zhao, K. J. Am. Chem. Soc. 1990, 112, 5875-5876. DOI
Keywords: O-H → O-SiMe2tBu • O-SiMe2tBu → O-H • CarboxEster → CarboxAmide • O-H → O-C(O)R • N-H → N-Alkyl(2°) • Amine-6 • O-C(O)R → O-H • B-Allyl-Ipc+Aldehyde • Aldol-B-Ipc • CarboxEster enolate+Epoxide • Epoxide+Enolate • Lactone-5 • Mechanism • Ozonolysis • Wittig-iodomethyl • Hofmann rearrangement • CarboxAmide → Amine • C-CO2H → C-N • Pd-Sonogashira • Si-Alkynyl → H-Alkynyl •
Reagents: SiMe2tBu-Cl • O3 • PPh3 • NaN(SiMe3)2 • HMPA (solvent) • HCl, H2O • PPh3, CBr4 • Chloride, ammonium • AlMe3 • DMAP • NEt3 • CuI • Fluoride, R4N+ • Carbonate, potassium • Chiral auxiliary-Boronate • Alkyl-B • Allyl-B(Ipc)2 • LiNiPr2

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