Total synthesis of Ibogamine (Sallay):
| Reference: | Sallay, S. I. J. Am. Chem. Soc. 1967, 89, 6762-6763. DOI |
| Reactions: | CompNu-Amine/Alkyl-OH+RC(O)X • Ketone → Ketal • CompE+-Ketone/Ketone+glycol • Ketone → Oxime • Beckman rearrangement • Lactam-7 • Bicyclo(540)-aza • Epoxidation, peracid • Epoxide reduction • CompRed-Epoxide/CarboxAmide+M-H • Alkyl-OH → Ketone • Wittig-methyl • Hydroboration → Alkyl-OH • CompRed-Alkene/Carboxamide+M-H • N-C(O)R → N-CH2R • Ketal → Ketone • N-H → N-Alkyl • Amine-6 • Bicyclo(222)-aza • Fischer Indole • Indole synthesis • |
| Reagents: | Glycol • NH2OH • TsCl, Py • Perbenzoic acid • AlH4-Li+ • PPh3=CH2 • BH3 • AlH4-Li+ • O=C(OBn)Cl (Cbz) • TsCl • HBr • Acetic acid • Hydrazine, phenyl • CrO3·Py2 (Collins) • |