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Total synthesis of Strychnine:
Reference: Ohshima, T.; Xu, Y.; Takita, R.; Shimizu, S. Zhong, D.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14546-14547. DOI
Keywords: Ketone → Ketal • EnoateEster → Allyl-OH • O-H → O-SiiPr3 • Ketal → Ketone • Ketone epimerization • O-H → O-SEM • O-SiiPr3 → O-H • O-H → O-Tf • Imine → Amine • O-PMB → O-H • O-SEM → O-H • Alkyl-OH → Aldehyde • Claisen acylation, Weinreb • CarboxEster enolate+CarboxAmide • CarboxAmide(Weinreb)+Enolate • Enone enolate+Aldehyde • O-H → O-SiiPr3 • Ether-7 • O-H → O-C(O)R • N-H → N-C(O)R • O-C(O)R → O-H • Saegusa oxidation • Ketone → Enone • Decarboxylation Krapcho • N-H → N-Allyl • Hydrogenolysis C-S • Ketone enamine+Thionium • Indole synthesis • Mechanism • Amine-6 • Mukaiyama Aldol • Aldol-Si • Dehydration → Enoate • Lactam-6 • O-H → O-SiiPr3 • Michael(asym) Enone • Enone → Enone-α-Halo • Pd/Sn-Aryl+Vinyl-X • Stille coupling • Ether-7 •
Reagents: Chloride, lithium • LiNiPr2 • Weinreb acetamide • BH3CN-Na+ • Carbodiimide • AlHiBu2 • SiiPr3-OTf • Camphor sulfonic acid • LiTMP • Pd2(dba)3 • LiNiPr2 • Formaldehyde • DBU • SEM-Cl • HF·NEt3 • Tf2O • Chloride, ammonium • Me2S-SMe+ X- • BH4-Na+, TiCl4 • HCl, H2O • NiCl2 • DMSO, Py·SO3 (Parikh-Doering) • NaOMe • Malonic acid • HF·NEt3 • Acetic anhydride • Yb(OTf)3 • NaOMe • O=C(OR)2 • CuCl • BH4-Na+ • NEtiPr2 • TiCl4 • SiMe3-Cl • SiMe3-Cl • Acetic anhydride • SiiPr3-Cl • Imidazole • DMSO (solvent) • Malonate • Chiral catalyst • KOtBu • I2 • AsPh3 • Aryl-SnR3 • DMAP •

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