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Total synthesis of Lepadiformine:
Reference: Sun, P.; Sun, C.; Weinreb, S. M. J. Org. Chem. 2002, 67, 4337. DOI
Keywords: N-H → N-Cbz • Aldehyde → Acetal • N-Cbz → N-H • Acetal → Aldehyde • O-Bn → O-H • Li/I → Li-Alkyl • Si-Alkyl → HO-Alkyl • Li-Alkyl+CarboxAmide • CarboxAmide+Li-R • Mg-Alkyl+Iminium • Iminium+Mg-R • Hydroformylation • CyanoAmine • Aldehyde → Enamine • Amine-6 • Si-Allyl+Iminium • Iminium+Si-R • O-H → O-Bn •
Reagents: Cu(SiMe2Ph)2Li • CuCN • CbzCl • Alkyl-Li • BuLi(tert) • BF3 • H2O2, NaHCO3 • Rh(CO)2acac • CO • Orthoformate • Na°/NH3 • Benzyl-X • TsOH • HCl, MeOH • Alkyl-MgX • BF3·OEt2 • Na°/NH3 • Cyanide, potassium • KH • Allyl-SiR3 • BF3 • NaH •

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