Total synthesis of Strychnofoline:
| Reference: | Lerchner, A.; Carreira, E. M. J. Am. Chem. Soc. 2002, 124, 14826. DOI |
| Reactions: | Selenide → Selenoxide • O-SiPh2tBu → O-H • Selenoxide-Ei → EneLactam • Lactam → EneLactam • Pictet-Spengler • Amine-6 • CarboxAmide → EnAmine • Cu-Allyl+EneLactam • ConjAdd Cu-Allyl • Mg-R → Cu-R • Cyclopropane alkylation • Spiro(44) • Bicyclo(430)-aza • Amine-5 • Wittig-methyl • Alkyl-OH → Aldehyde • CompOx-Alkyl-OH/Amine+IBX • Acetal → Aldehyde • N-Boc → N-H • Alkene → Diol-1,2 • Diol-1,2 cleavage • Alkene cleavage • Aldehyde → Acetal(Me) • Lactam → Lactam-α-SeR • |
| Reagents: | LiN(SiMe3)2 • H2O2 • Allyl-MgX • SiMe3-Cl • AlHiBu2 • SiMe3-OTf • NEt3 • OsO4, NMO • Periodate, sodium • Orthoformate • Fluoride, R4N+ • IBX • PPh3=CH2 • HCl, H2O • Acetic acid • SePh-Cl • CuBr·SMe2 • DMSO (solvent) • MgI2 • HCl, H2O • |