Total synthesis of Elisapterocin B:
| Reference: | Waizumi, N,; Stankovic, A. R.; Rawal, V. H.J. Am. Chem. Soc. 2003, 125, 13022. DOI |
| Reactions: | Lactone enolate+Alkyl-X • Alkyl-X+Enolate • CarboxCl+Zn-R • Zn-Aryl+CarboxCl • CompRed-Alkene/Alkene+H2 • Hydrogenation Alkene • Cationic cyclization • Cyclopentanone • Bicyclo(321) • Alkyne → Vinyl-Br • Quinone synthesis • Phenol → Quinone • Pd/Mg-Aryl+CarboxCl • Mg-R → Zn-R • Li/Br → Li-Vinyl • Li-R → Zn-R • Seyferth-Gilbert homologation • Aldehyde → Alkyne • Ketone → Ketal(Me) • Diels-Alder, Intram, Ene • Diels-Alder, Quinone • Cyclopentane • Bicyclo(440) • Bicyclo(430) • Pinacol • Phenonium • Lactone → Lactol • Alkyne → Alkynyl-Br • CarboxEster → Aldehyde • Pd/Zn-Vinyl+Vinyl-X • Wittig-isopropyl • O-Me → O-H (phenol) • Diimide+Alkyne • |
| Reagents: | Aryl-MgX • Orthoformate • NaN(SiMe3)2 • MeI • AlHiBu2 • Diazophosphonate • AgNO3 • NBS • Hydrazine, tosyl • Acetate, sodium • Propenyl-ZnX • BuLi(tert) • PdCl2(dppf) • AlHiBu2 • PPh3=CMe2 • Thiolate, ethyl • O2 • Salcomine • Iodide, lithium • Ceric ammonium nitrate • H2, Rh • PdCl2(PPh3)2 • ZnCl2 • Diimide • KOtBu • DMF (solvent) • Sulfonyl chloride, methane • Carbonate, calcium • Salcomine • Lutidine • |