Total synthesis of Deplancheine:
| Reference: | Overman, L. E.; Malone, T. C. J. Org. Chem. 1982, 47, 5297. DOI |
| Reactions: | Acetal → Aldehyde • Pictet-Spengler • Amine-6 • Hydroalumination Alkyne • Li-Vinyl+Alkyl-X • Alkyl-X+Li-R • Pictet-Spengler • Amine-6 • Alkene isomerization-EZ • Si-Vinyl+Iminium • Iminium+Si-R • Amine-6 • Bicyclo(440)-aza • Si-Vinyl+Iminium • Iminium+Si-R • Amine-6 • Al-Vinyl → Br-Vinyl • Alkyne → Vinyl-Br • Li/Br → Li-Vinyl • |
| Reagents: | Alkynyl-SiR3 • AlHiBu2 • Vinyl-SiR3 • Vinyl-Li • BuLi(sec) • HCl, THF • Formaldehyde • NBS • HCl, H2O • Photochemistry • Formaldehyde • Sulfonic acid, Camphor • |