image

Total synthesis of Gephyrotoxin:
Reference: Shirokane, K.; Wada, T.; Yoritate, M.; Minamikawa, R.; Takayama, N.; Sato, T.; Chida, N. Angew. Chem. Int. Ed. 2014, 53, 512-516 DOI
Keywords: CompE+-CarboxAmide/CarboxEster+M-H • CompE+-CarboxEster/CarboxEster+Al-H • Aldehyde → Alkyl-OH • CarboxAcid → CarboxAmide • Olefin cross metathesis • Si-Allyl+Iminium • Iminium+Si-R • Ozonolysis • HWE → EnoateEster-cis • Radical cyclization(Alkyl) • Sn-Allyl+Iminium • Iminium+Sn-R • Hydroboration alkene • CompE+-Alkene/CarboxEster+B-H • HWE → EnoateEster • ConjAdd Amine • N-OR → N-H • CarboxEster → Aldehyde • Wittig-iodomethyl • Pd-Sonogashira • CarboxEster → Aldehyde • CompRed-CarboxEster/Alkyne • Lactam-6 • Amine-5 •
Reagents: NH2OMe • Carbodiimide • Grubbs II • Allyl-SiR3 • BF3·OEt2 • Me2S • DBU • HSnBu3 • ZrCp2ClH • Allyl-SnR3 • BH2(Thexyl) • NaBO3 • AlH(OR)2iBu-Na+ • PPh3=CH-R • NaN(SiEt3)2 • Pd(PPh3)4 • CuI • AlHiBu2 • BH4-Na+ • DMSO, Py·SO3 (Parikh-Doering) • AIBN •

Syntheses Home