Total synthesis of Staphacidin:
| Reference: | Herzon, S. B.; Myers, A. G J. Am. Chem. Soc. 2005, 127, 5342 DOI |
| Reactions: | Lactam-6 • O-SiPh2tBu → O-H • Enone → Enone-α-Halo • Ullman coupling • Ketone enolate+Me-I • Alkyl-X+Enolate • EnAmine → CyanoAmine • Cyanoamine • Ketone epimerization • Nitrile → CarboxAmide • Nitrone synthesis • Radical cyclization(Acyl) • Bicyclo(222)-aza • ConjAdd M-SR • Enone+Thiolate • Lactam-6 • Spiro(54) • Saegusa oxidation • Ketone → Enone • Ketone → EnolSilane • Enone enolate+Alkyl-X • Allyl-X+Enolate • O-H → O-SiPh2tBu • Ketal → Enone • CompNu-Ketal/SiO+H+ • Ketone → EnAmine • N-H → N-C(O)R • Bicyclo(440)-aza • Allyl-OH → Enone • Ketone → Alkyl-OH (asym) • N-Boc → N-H • |
| Reagents: | LiN(SiMe3)2 • SiMe3-Cl • Pd(OAc)2 • BH3·SMe2 • 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 • Chiral catalyst (amino-alcohol) • Corey oxazaborolidine • |