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Total synthesis of Staphacidin:
Reference: Herzon, S. B.; Myers, A. G J. Am. Chem. Soc. 2005, 127, 5342 DOI
Keywords: Saegusa oxidation --- Ketone -> Enone --- Ketone -> Alkyl-OH(asym) --- O-H -> O-SiPh2tBu --- Ketone -> Ketal --- Enone enolate+Allyl-X --- ConjAdd M-SR --- Lactam-6 --- Ketone -> Enamine --- N-Boc -> N-H --- O-SiPh2tBu -> O-H --- Allyl-OH -> Enone --- Enone -> Enone-α-Halo --- Ullman coupling --- Ketone enolate+Me-I --- Enamine -> CyanoAmine --- Ketone epimerization --- Nitrile -> CarboxAcid --- Radical cyclization(Acyl) --- Nitrone synthesis
Reagents: LiN(SiMe3)2 --- SiMe3-Cl --- Pd(OAc)2 --- BH3·SMe2 --- Corey oxazaborolidine --- SiPh2tBu-OTf --- Lutidine --- H2SO4 --- KN(SiMe3)2 --- Cyanide, trimethylsilyl --- KN(SiMe3)2 --- NaOtBu --- MeI --- Piv-OH --- HS-Ph --- NEt3 --- SiMe3-OTf --- Lutidine --- HF --- Dess-Martin --- I2 --- DMAP --- Pd2(dba)3 --- Zn° --- NEtiPr2 --- NEt3

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