Total synthesis of Vindorosine:
| Reference: | Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. DOI |
| Reactions: | N-H → N-C(O)R • N-C(O)R → N-H • ConjAdd Amine • ConjAdd EnAmine • Amine-5 • Mechanism • Cyclohexanone • Bicyclo(430)-aza • ConjAdd Amine • Aldol-Na → Aldol • Ketone enolate+Aldehyde • Amine-6 • Bicyclo(440)-aza • Ketone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • Claisen acylation, carbonate • CarboxEster enolate+Carbonate • CarboxEster → CarboxEster-α-OR • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • O-H → O-C(O)R • CompNu-O-H/O-H+RC(O)X • |
| Reagents: | Methyl vinyl ketone • NEt3 • Acetic anhydride, NEt3 • HCl, H2O • BF3 • Acrolein • NaOMe • BF3 • KOtBu • O=C(OR)2 • NaH • H2O2 • AlH4-Li+ • Acetic anhydride • |