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Total synthesis of Cuauhtemone:
Reference: Goldsmith, D. J.; Sakano, I. J. Org. Chem. 1976, 41, 2095. DOI
Keywords: Ketone -> Vinyl-OP(O)(OR)2 • Ketal -> Ketone • Alkene -> Diol-1,2 • Diol -> Ketal • Ketone enamine+Alkyl-X • ConjReduct-Phosphorylation • Enone ConjReduct • Claisen acylation, carbonate • Ketone enolate+Carbonate • Vinyl-OP(O)(OR)2 -> Vinyl-H • Enone -> Alkene • Li-Me+CarboxEster • CarboxEster+Li-R • Protecting group - Ketone • Dehydration -> Enone • Robinson annulation, ketone • Ketone enamine+Enone • Enone+Enamine •
Reagents: Pyrrolidine • MeI • Li°/NH3 • P(O)(OR)2Cl • Li°/NH3 • OsO4 • Acetone (react) • CuSO4 • O=C(OR)2 • NaH • NaH • SOCl2 • Acetic acid • MeLi • Ethyl vinyl ketone • Hydroxide, potassium • Pyrrolidine •

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