Total synthesis of Adaline:
| Reference: | Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. DOI |
| Reactions: | Barton-McCombie reduction • Alkyl-OH → Alkyl-H(2°) • Si-Allyl+Iminium • Iminium+Si-R • Li-Alkynyl+Iminium • Iminium+Li-R • Li/H → Li-Alkynyl • Alkyne → Ene-cis (Lindlar) • N-H → N-C(O)H • CarboxAmide → Alkyl-OH • CarboxAcid → CarboxAmide • Lactam-6 • Ketone → Aminal • RCM → Ring-N • Amine-6 • Bicyclo(331)-aza • Alkyl-OH → Aldehyde • Amine-6 • Aldehyde → Aminal • Alkene → Diol-1,2 • O-H → O-SiMe2tBu • CompNu-O-H/O-H+R3Si-X • O-H → O-C(S)SR • Alkyl-OH → Ketone • CompOx-Alkyl-OH/Amine+CrO3 • N-Bn → N-H • N-C(O)R → N-H • O-SiMe2tBu → O-H • |
| Reagents: | TiCl4 • Allyl-SiR3 • BH3NH2-Li+ • RuO4-Pr4N+, NMO • Alkynyl-Li • Orthoformate • TsOH • H2, Pd • OsO4, NMO • SiMe2tBu-OTf • CS2 • HSnBu3 • Fluoride, R4N+ • Li°/H2NCH2CH2NH2 • CrO3Cl·PyH (PCC) • AIBN • Grubbs II • |