Total synthesis of Coriolin (Kuwajima) New:
| Reference: | Mizuno, H.; Domon, K.; Masuya, K.; Tanino, K.; Kuwajima, I. J. Org. Chem. Soc. 1999, 64, 2648-2656. DOI |
| Reactions: | Radical reduction(C-SR) • Hydrogenation Enone • Nitrile anion+Alkyl-X • Alkyl-X+Nitrile anion • Nitrile+Li-R → Ketone • Li-Sulfide+Nitrile • Acetal → Aldehyde • Aldol-Na → Enone • Cyclopentenone • Enone → Allyl-OH • O-H → O-Bn • 3+2 Annulation • Allyl cation Cycloaddition • Cycloaddition Oxyallyl • Cyclopentanone • 3+2 Annulation • Allyl cation Cycloaddition • Cycloaddition Oxyallyl • Cyclopentanone • Ketone → EneSulfide • Dehydrosulfidation → Enone • ConjAdd M-SR • Ketone-α-SR → Ketone • Dehydrosulfidation → Enone • O-Bn → O-H • O-H → O-SiMe3 • Ketone → EnolSilane • Epoxidation, peracid • EnolSilane → Ketone • Dehydroalkoxylation → Enone • O-H → O-SiMe3 • Aldol-Li → Aldol • Ketone enolate+Aldehyde • Ketone enolate+I2 • Epoxidation via halohydrin • Darzens • O-SiMe3 → O-H • Enone epoxidation, nucleophilic • |
| Reagents: | LiNiPr2 • HMPA (solvent) • Acetic acid • H2SO4 • Hydroxide, sodium • AlHiBu2 • Lipase • Benzyl-X • NaH • AlEtCl2 • HSnBu3 • AIBN • H2, Pd • SiMe3-Cl • AlEtCl2 • Fluoride, R4N+ • Hydroxide, sodium • B(Br)3 • SiMe3-Cl • KH • SiiPr3-Cl • Oxone • Acetic acid • SiMe3-Cl • LiNiPr2 • Formaldehyde • LiNiPr2 • NIS • HF·Py • H2O2, NaHCO3 • |