Total synthesis of Platensimycin (Nicolaou):
| Reference: | Nicolaou, K. C.; Li, A.; Edmonds, D. J.; Tria, G. S.; Ellery, S. P. J. Am. Chem. Soc. 2009, 131, 16905. DOI |
| Reactions: | O-SiMe2tBu → O-H (phenol) • Ether-5 • CarboxEster → CarboxAcid • O-MOM → O-H • CarboxAcid → CarboxAmide • CarboxAmide enolate(Myers)+Alkyl-X • Benzyl-X+Enolate (asym) • 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 • Spiro(54) • Ketyl+Enone • Cyclohexane • Bicyclo(321) • Alkene hydration • Ether-5 • Ether-5 • Bicyclo(330)-oxa • Bicyclo(321)-oxa • Mg-Silane • CarboxAcid → CarboxAmide • CarboxEster → CarboxAcid • |
| Reagents: | Piv-Cl • Pseudoephedrine • LiNiPr2 • Benzyl-X • Me-Li • KN(SiMe3)2 • Tf2N-2-Py-5-Cl • 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, H2O • Iodosobenzene-OAc • CF3CH2OH (solvent) • HCl, H2O • SmI2 • HMPA (solvent) • Hexafluoroisopropanol (solvent) • Chiral auxiliary (amide-Myers) • |