Total synthesis of Histrionicotoxin (Fuchs):
| Reference: | Karatholuvho, M. S.; Sinclair, A.; Newton, A. F.; Alcaraz, M.-L.; Stockman, R. A.; Fuchs. P. L. J. Am. Chem. Soc., 2006, 128, 12656. DOI |
| Reactions: | Olefin cross metathesis • Mg-Alkyl+CarboxEster • Formate+Mg-R • Nitrile → Aldehyde • Dehydrohalogenation → Vinyl-X • Wittig-alkyl → Ene-cis • Alkynyl-Cl → Alkynyl-H • Dehydrohalogenation → Alkynyl-Cl • Nitrone Cycloaddition • Spiro(54)-aza • Nitrone Retro-cycloaddition • Retro-1,3-dipolar cycloaddition • Cyclohexane • Ketone → Nitrone • ConjAdd Amine • Amine-6 • Alkyl-OH → Ketone • N-OR → N-H • |
| Reagents: | Alkyl-MgX • Mg° • Formate, ethyl • Grubbs-Hoveyda • Acrylonitrile • AlHiBu2 • PPh3=CH-Alkyl • DBU • NaN(SiMe3)2 • CrCl2 • Thiol, propyl • NaN(SiMe3)2 • Acrylonitrile • CrO3Cl·PyH (PCC) • NH2OH • |