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Total synthesis of Staphacidin:
Reference: Herzon, S. B.; Myers, A. G J. Am. Chem. Soc. 2005, 127, 5342 DOI
Keywords: Lactam-6 • O-SiPh2tBu → O-H • Enone → Enone-α-Halo • Ullman coupling • Ketone enolate+Me-I • EnAmine → CyanoAmine • Cyanoamine • Ketone epimerization • Nitrile → CarboxAmide • Nitrone synthesis • Radical cyclization(Acyl) • Bicyclo(222) • ConjAdd M-SR • Lactam-6 • Saegusa oxidation • Ketone → Enone • Enone enolate+Alkyl-X • Alkyl-X+Enolate • O-H → O-SiPh2tBu • Ketal → Enone • Ketone → EnAmine • N-Boc → N-H • N-H → N-C(O)R • Allyl-OH → Enone • Ketone → Alkyl-OH(asym) •
Reagents: LiN(SiMe3)2 • SiMe3-Cl • Pd(OAc)2 • BH3·SMe2 • Corey oxazaborolidine • SiPh2tBu-OTf • Lutidine • H2SO4 • KN(SiMe3)2 • Cyanide, trimethylsilyl • Hexafluoroisopropanol (solvent) • KN(SiMe3)2 • NaOtBu • MeI • Piv-OH • Thiol, phenyl • NEt3 • SiMe3-OTf • Lutidine • HF • Dess-Martin • DMAP • Pd2(dba)3 • Zn° • NEtiPr2 • NEt3

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