Total synthesis of Nopinone New:
| Reference: | Thomas, M. T.; Fallís, A. G. J. Am. Chem. Soc. 1973, 98, 1227-1231. DOI |
| Reactions: | Ketone → Ketal(thio) • CarboxEster → Alkyl-OH • O-H → O-C(O)R • Ketal(thio) → Ketone • ConjAdd Cu-Me • Cu-Me+Enone • Aldol-K → Enone • Ketone enolate+Aldehyde • O-H → O-SO2Ar • Ketone enolate+Alkyl-X (intram) • Retro-Aldol • Wittig-methyl • |
| Reagents: | Hagemann's ester • Thiol, (CH2)2-SH • BF3·OEt2 • AlH4-Li+ • Me-Cuprate • Acetic anhydride, Py • HgCl2 • Hydroxide, potassium • TsCl, Py • NaH • Acetonitrile (solvent) • Hydroxide, potassium • DMSO (solvent) • PPh3=CH2 • |