Total Syntheses

Reaction scheme for total synthesis of the natural product Aspidospermine Model
Total synthesis of Aspidospermine Model:
Reference:Magnus, P.; Cairns, P. M.; Kim, C. S. Tetrahedron Lett., 1985, 26, 1963. DOI
Reactions:Retro-Diels-Alder → Alkene • Pummerer • Amine-5 • Bicyclo(430)-aza • Singlet oxygen+Diene • Furan+Singlet oxygen • Diels-Alder, Intram, o-Xylylene • Lactam-6 • Decarboxylative elimination • Aldehyde → Imine • CarboxAcid → CarboxAmide • Lactam-6 • Wittig-methyl • Diels-Alder, EnoateEster • Bicyclo(221) • CarboxAcid → CarboxCl • Sulfide → Sulfoxide •
Reagents:Perbenzoic acid, 3-chloro • Acetic anhydride, trifluoro • O2 (singlet) • PPh3=CH2 • Oxalyl chloride • Cyclopentadiene •