Total synthesis of Cuauhtemone:
| Reference: | Goldsmith, D. J.; Sakano, I. J. Org. Chem. 1976, 41, 2095. DOI |
| Reactions: | Ketone → EnolPhosphate • Ketone enamine+Alkyl-X • Alkyl-X+EnAmine • ConjReduct-Phosphorylation • Enone ConjReduct • Claisen acylation, carbonate • Ketone enolate+Carbonate • EnolPhosphate → Vinyl-H • Enone → Alkene • Li-Me+CarboxEster • CarboxEster+Li-R • Protecting group - Ketone • Dehydration → Enone • Robinson annulation, ketone • Ketone enamine+Enone • Enone+EnAmine • Cyclohexenone • Bicyclo(440) • Diol-1,2 → Ketal • Alkene → Diol-1,2 • Ketal → Ketone • |
| Reagents: | Pyrrolidine • MeI • Li°/NH3 • P(O)(OR)2Cl • Li°/NH3 • OsO4 • Acetone (react) • CuSO4 • O=C(OR)2 • NaH • NaH • SOCl2 • Acetic acid • Me-Li • Ethyl vinyl ketone • Hydroxide, potassium • Pyrrolidine • |