Total synthesis of Coleophomone D:
| Reference: | Nicolaou, K. C.; Montagnon, T.; Vassilikogiannakis, G.; Mathison, C. J. N. J. Am. Chem. Soc. 2005, 127, 8872. DOI |
| Reactions: | Selenide → Selenoxide • Selenoxide-Ei → Dienone • Ketone → Enone • Enone enolate+Alkyl-X • Allyl-X+Enolate • Claisen acylation, Mander • Enone enolate+Mander • Mander+enolate • Aldehyde → Cyanohydrin • Benzyl-OH → Aldehyde • Ketone → Ketone-α-SeR • Cyanohydrin → AcylCyanide • EnolEther → Ketone • O-C(O)R → O-H • Spiro(45) • |
| Reagents: | LiNiPr2 • LiNiPr2 • LiNiPr2 • H2O2 • Hydroxide, lithium • Cyanide, AlR2 • CrO3Cl·PyH (PCC) • NEt3 • Carbonate, potassium • MnO2 • Allyl-Br • SePh-Cl • |