image

Total synthesis of Adaline:
Reference: Itoh, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469. DOI
Keywords: Alkyl-OH → Aldehyde • Amine-6 • N-H → N-C(O)H • Alkene → Diol-1,2 • O-H → O-SiMe2tBu • O-H → O-C(S)SR • O-SiMe2tBu → O-H • N-CHO → N-H • Alkyl-OH → Ketone • Barton-McCombie reduction • Alkyl-OH → Alkyl-H • Si-Allyl+Iminium • Iminium+Si-R • Li-Alkynyl+Iminium • Iminium+Li-R • Li/H → Li-Alkynyl • Hydrogenation Lindlar • N-H → N-C(O)H • CarboxAmide → Alkyl-OH • CarboxAcid → CarboxAmide • Lactam-6 • RCM → Ring-N • Amine-6 •
Reagents: TiCl4 • Allyl-SiR3 • BH3NH2-Li+ • RuO4-Pr4N+, NMO • Alkynyl-Li • Orthoformate • TsOH • H2, Pd • OsO4, NMO • NEt3 • CS2 • HSnBu3 • Fluoride, R4N+ • Li°/H2NCH2CH2NH2 • CrO3Cl·PyH (PCC) • AIBN • Grubbs II •

Syntheses Home