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Total synthesis of Retronecine:
Reference: Tufariello, J. J.; Lee, G. E. J. Am. Chem. Soc. 1980, 102, 373. DOI
Keywords: Ketone → Ketal(Me) • N-R → N-OH • Hydroxylamine → Nitrone • O-H → O-SO2R • Ketal → Ketone • Ketone → Alkyl-OH • EnoateEster → Allyl-OH • Hydrogenolysis N-O • Amine-5 • N-H → N-Alkyl • Dehydration → Enoate • Cope elimination • CompRed-Ketone/CarboxEster+B-H • Nitrone Cycloaddition •
Reagents: Orthoformate • HCl, MeOH • HgO • Sulfonyl chloride, methane, NEt3 • H2, Pd • Sulfonyl chloride, methane • NEt3 • HCl, H2O • BH4-Na+ • AlH3

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