Total synthesis of Nitidasin (Part 1) New:
| Reference: | Daniel T. Hog, D.T.; Florian M. E. Huber, F. M. E.; Peter Mayer, P.; Trauner, D. Angew. Chem. Int. Ed. 2014, 53, 8513-8517 DOI (Part 2) |
| Reactions: | O-SiEt3 → O=H • O-But → O-H • Ketone → Ketal • Alkyl-OH → Ketone • Ketone → EnolSilane • Saegusa oxidation • Ketone → Enone • Cu-Alkyl+Enone • Enone+Cu-R • ConjAdd Cu-Alkyl • Mg-R → Cu-R • Hydrogenation Alkene • Ketone → EnolTriflate • EnolTriflate → Vinyl-H • Ketone → Alkene • Hydroboration → Alkyl-OH • Ketal → Ketone • O-H → O-SEM • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Ketone → Alkyl-OH • Alkene cleavage • Lemieux-Johnson oxidation • Lactol → Lactone • Lactone enolate+Alkyl-X • Alkyl-X+Enolate • Lactone → Alkyl-OH • O-H → O-SiEt3 • Alkyl-OH → Aldehyde • Wittig-methyl • Alkyl-OH → Ketone • |
| Reagents: | HCl, H2O • Glycol • Cr2O7·2PyH (PDC) • LiNiPr2 • SiMe3-Cl • Pd(OAc)2 • CuCN • Propenyl-MgX • KN(SiMe3)2 • Tf2NPh • H2, Pt • PdCl2 • Formic acid • NBu3 • BH2(Ipc) • H2O2, NaOH • SEM-Cl • TsOH·Py • KN(SiMe3)2 • BEt3 • Allyl-Br • Pd(PPh3)4 • BH(sBu3)-K+ • OsO4, NaIO4 • CrO3 • AlH4-Li+ • SiEt3-Cl • LiN(SiMe3)2 • MeI • DMSO, (COCl)2 (Swern) • NEt3 • PPh3=CH2 • Sulfonic acid, Camphor • Dess-Martin • |