Total synthesis of Retronecine (Tufariello):
| Reference: | Tufariello, J. J.; Lee, G. E. J. Am. Chem. Soc. 1980, 102, 373. DOI |
| Reactions: | Ketone → Ketal(Me) • N-R → N-OH • N-OR → N-H • N-H → N-Alkyl • Amine-5 • Bicyclo(330)-aza • Dehydration → Enoate • Cope elimination • Ketone → Alkyl-OH • CompRed-Ketone/CarboxEster+M-H • Nitrone Cycloaddition • Ketone → Ketal(Me) • Hydroxylamine → Nitrone • O-H → O-SO2Me • Ketal → Ketone • EnoateEster → Allyl-OH • |
| Reagents: | Orthoformate • HCl, MeOH • HgO • Sulfonyl chloride, methane, NEt3 • H2, Pd • Sulfonyl chloride, methane • NEt3 • HCl, H2O • BH4-Na+ • AlH3 • Crotonate • HOMe (react) • |