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Total synthesis of Platensimycin:
Reference: Nicolaou, K. C.; Li, A.; Edmonds, D. J.; Tria, G. S.; Ellery, S. P. J. Am. Chem. Soc. 2009, 131, 16905. DOI
Keywords: O-SiMe2tBu → O-H (phenol) • Ether-5 • CarboxEster → CarboxAcid • O-MOM → O-H • CarboxAcid → CarboxAmide • CarboxAmide enolate(Myers)+Alkyl-X • Alkyl-X+Enolate • CarboxAmide → Ketone • Li-Me+CarboxAmide • CarboxAmide+Li-R • Ketone → EnolTriflate • Enone enolate+Alkyl-X • Alkyl-X+Enolate • ConjAdd Enolate • Enone enolate+EnoateEster • Acetal → Aldehyde • Pd/Mg-Alkyl+Vinyl-X • Si-Allyl+Oxonium • Cyclopentane • Ketyl+Enone • Cyclohexane • Alkene hydration • Ether-5 • Ether-5 • Mg-Silane • CarboxEster → CarboxAmide • CarboxEster → CarboxAcid •
Reagents: Piv-Cl • Ephedrine • LiNiPr2 • MeLi • KN(SiMe3)2 • MgCH2-SiMe3 • Pd(PPh3)4 • Chloride, lithium • Hydroxide, sodium • Acetic acid, trifluoro • KN(SiMe3)2 • MeI • Acrylate • KOtBu • Acetic acid, trifluoro • HATU • Hydroxide, lithium • HCl • Iodosobenzene-OAc • CF3CH2OH(solvent) • HCl, H2O • SmI2 • HMPA (solvent) • Hexafluoroisopropanol (solvent) • Chiral auxiliary-Myers • HMPA (solvent) •

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