Total synthesis of Aloperine, iso:
| Reference: | Brosius, A. D.; Overman, L. E. J. Org. Chem. 1997, 62, 440. DOI |
| Reactions: | Epoxide+M-SeR • Selenolate+Epoxide • N-Boc → N-H • N-C(O)OR → N-H • Selenoxide-Ei → Allyl-OR • Epoxide → Allyl-OH • Pd/B-Alkyl+Vinyl-X • Dehydrohalogenation → Ene • Dehydration → Ene • N-C(O)R → N-CH2R • Furst-Plattner diaxial • Epoxidation, peracid • ConjAdd Amine • Amine-6 • Bicyclo(440)-aza • Alkene Carboiodination • Amine-6 • Bicyclo(331)-aza • Allyl-OH → Enone • Enone → Enone-α-Halo • Ketone → Alkyl-OH • N-H → N-C(O)OR • |
| Reagents: | DBU • Selenolate, phenyl • H2O2 • RuO4-Pr4N+, NMO • I2 • Vinyl-I • Alkyl-BR2 • PdCl2(dppf) • Acetic acid, trifluoro • Hydroxide, sodium • AlH4-Li+ • O=C(OCH2CCl3)Cl (Troc) • O=C(OCH2CCl3)Cl (Troc) • POCl3 • Cd/Pb • TfOH • Iodide, R4N+ • RuO4-Pr4N+ • Perbenzoic acid, 3-chloro • |