Total synthesis of Dendrobine (Kende):
| Reference: | Kende, A. S.; Bentley, T. J.; Mader, R. A.; Ridge, D. J. Am. Chem. Soc. 1974, 96, 4332-4334. DOI |
| Reactions: | Diels-Alder, Quinone • Bicyclo(440) • Enol → EnolEther • Quinone synthesis • Cu-Vinyl+Enone • Enone-β-OR → Enone • Enone-β-OR+Al-H • Stork-Danheiser • CarboxEster epimerization • Ketone epimerization • Reductive amination, B-H • Alkene cleavage • CarboxAcid → CarboxEster • Amine-5 • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Lactone-5 • Alkene → Diol-1,2 • Diol-1,2 cleavage • Aldol-enamine → Enone • Cyclopentene • Bicyclo(430) • O-C(O)R → O-H (phenol) • |
| Reagents: | Hydroxide, potassium • FeCl3 • Carbonate, potassium • Ba(ClO3)2 • Pyrrolidine • Periodate, sodium • AlH4-Li+ • H2SO4 • Vinyl-Cu • RuO4 • Diazomethane • NaOMe • BH4-Na+ • Butadiene • BH3CN-Na+ • NH2Me • |