Total synthesis of Lardolure:
| Reference: | Mazery, R. D.; Pullez, M.; Lopez, F.; Harutyunyan, S. R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2005, 127, 9966. DOI |
| Reactions: | Cu-Me+EnoateEster • ConjAdd Cu-R (asym) • Mg-R → Cu-R • Wittig-carboxymethyl → EnoateEster • Li-Sulfoxide+CarboxEster(thio) • CarboxEster(thio)+Li-R • Hydrogenolysis Acyl-SR • CarboxEster(thio) → Aldehyde • Hydrogenolysis Acyl-SR • CarboxEster(thio) → Aldehyde • Alkyl-S(O)R → Alkyl-H • Wittig-carboxymethyl → EnoateEster • Cu-Me+EnoateEster • ConjAdd Cu-R (asym) • Mg-R → Cu-R • Ketone → Alkyl-OH • O-H → O-C(O)R • |
| Reagents: | Me-MgBr • CuBr·SMe2 • HSiEt3, Pd • PPh3=CH-C(O)SEt • Me-MgBr • CuBr·SMe2 • PPh3=CH-C(O)SEt • Me-MgBr • CuBr·SMe2 • LiCH2-Sulfinyl • AlHiBu2 • ZnBr2 • RaNi • Formic acid • HSiEt3, Pd • Chiral catalyst (phosphine) • Chiral catalyst (phosphine) • |