image

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

Syntheses Home