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Total synthesis of Strychnofoline:
Reference: Lerchner, A.; Carreira, E. M. J. Am. Chem. Soc. 2002, 124, 14826. DOI
Keywords: CarboxAmide → Imine • N-Boc → N-H • Alkene → Diol-1,2 • Alkene cleavage • Diol-1,2 cleavage • O-SiPh2tBu → O-H • Alkyl-OH → Aldehyde • Acetal → Aldehyde • Selenoxide-Ei → EneLactam • Lactam → EneLactam • Pictet-Spengler • CarboxAmide → Enamine • Cu-Allyl+EneLactam • ConjAdd Cu-R • CarboxAmide → CarboxAmide-α-SeR • Aldehyde → Acetal(Me) • Alkyl-OH → Aldehyde • Cyclopropane alkylation • Amine-5 • Wittig-methyl •
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 • IBX •

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