Total synthesis of Gephyrotoxin (Chida):
| Reference: | Shirokane, K.; Wada, T.; Yoritate, M.; Minamikawa, R.; Takayama, N.; Sato, T.; Chida, N. Angew. Chem. Int. Ed. 2014, 53, 512-516 DOI |
| Reactions: | CompRed-CarboxAmide/CarboxEster+M-H • CompRed-CarboxEster/CarboxEster+M-H • Aldehyde → Alkyl-OH • CarboxAcid → CarboxAmide(Weinreb) • Olefin cross metathesis • Si-Allyl+Iminium • Iminium+Si-R • Ozonolysis • HWE → EnoateEster-cis • Radical cyclization(Alkyl) • Cyclohexane • Bicyclo(440)-aza • Sn-Allyl+Iminium • Iminium+Sn-R • Hydroboration → Alkyl-OH • CompRed-Alkene/CarboxEster+M-H • HWE → EnoateEster • Li-PhosphineOxide+Aldehyde • ConjAdd Amine • N-OR → N-H • CarboxEster → Aldehyde • Wittig-iodomethyl • Pd/H-Alkynyl+Vinyl-X • CarboxEster → Aldehyde • CompRed-CarboxEster/Alkyne+M-H • Lactam-6 • Amine-5 • Bicyclo(430)-aza • Si-Alkynyl → H-Alkynyl • Aldehyde → Alkyl-OH • CompOx-Alkyl-OH/Amine+DMSO • |
| Reagents: | Allyl-SiR3 • NH2OMe • Carbodiimide • Grubbs II • Allyl-SiR3 • BF3·OEt2 • O3 • DBU • HSnBu3 • ZrCp2ClH • Sc(OTf)3 • Allyl-SnR3 • BH2(Thexyl) • NaBO3 • NEtiPr2 • AlH(OR)2iBu-Na+ • PPh3=CH-I • NaN(SiEt3)2 • Alkynyl-SiR3 • Pd(PPh3)4 • CuI • AlHiBu2 • BH4-Na+ • DMSO, Py·SO3 (Parikh-Doering) • AIBN • HOBT • Carbonate, potassium • |