Total synthesis of Nominine:
| Reference: | Peese, K. M.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 8734. DOI |
| Reactions: | Diels-Alder, Intram, Ene • Bicyclo(222) • Azomethine ylide Cycloaddition • Amine-5 • Li-Aryl+CarboxAmide • CarboxAmide(Weinreb)+Li-R • Reductive amination, B-H • Azomethine ylide Retro-cycloaddition • Retro-1,3-dipolar cycloaddition • Bicyclo(321)-aza • Bicyclo(331)-aza • Radical reduction(C-Cl) • Ketone → CH2 • Alkyl-X → Alkyl-H(2°) • Birch reduction • Ketone → EnAmine • Allylic oxidation → Allyl-OH • Oxidopyridinium • ConjAdd M-CN • EnolTriflate → EneNitrile • Nitrile → Aldehyde • EnolEther → Ketone • Wittig-Methyl • Wittig-Methyl • Ketone → Alkyl-OH • CompRed-Ketone/Nitrile+M-H • Nitrile → Aldehyde • Alkyl-OH → Alkyl-Cl • Li/H → Li-Aryl • CompE+-Ar-H/Ar-H+Base • Alkyl-X → Alkyl-N3 • Azide → Amine • Staudinger • Ketone → Ketal(Me) • |
| Reagents: | Cyanide, AlR2 • Tf2O • AlHiBu2 • Cyanide, zinc • Pd(PPh3)4 • BuLi(tert) • Azide, sodium • Acetyl chloride • BH(OAc)3-Na+ • Acetic acid, trifluoro • PBu3 • BH4-Na+ • SOCl2 • HSnBu3 • AlHiBu2 • PPh3=CH2 • Na°, ROH • HCl, H2O • Butadiene • Pyrrolidine • PPh3=CH2 • SeO2 • Aryl-Li • AIBN • HOMe (react) • |