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

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