Total synthesis of Luciduline (Evans):
| Reference: | Scott, W. I.; Evans, D. A. J. Am. Chem. Soc. 1972, 94, 4779-4780. DOI |
| Reactions: | Ketal → Ketone • Mannich • Diels-Alder, EneNitrile • Bicyclo(222) • Cyanohydrin → Ketone • Mg-Vinyl+Ketone • Cope rearrangement • Bicyclo(440) • Ketone → Alkene • Shapiro reaction • Epoxidation, peracid • N-H → N-Alkyl (2°) • Ketone → Hydrazone • Epoxide+M-SR • Thiolate+Epoxide • Alkyl-SR → Alkyl-H • O-H → O-SO2Ar • Amine-6 • Ketone → Ketal • |
| Reagents: | Butadiene, 1-OR • Acrylonitrile • Hydroxide, potassium • Propenyl-MgX • Glycol • Hydrazine, tosyl • Me-Li • Perbenzoic acid, 3-chloro • Thiolate, phenyl • TsCl, Py • NH2Me • Formaldehyde • |