Reference: | Ling, T.; Chowdhury, C.; Kramer, B. A.; Vong, B. G.; Palladino, M. A.; Theodorakis, E. A. J. Org. Chem. 2001, 66, 8843. DOI |
Keywords: | Jones oxidation Allyl-OH → Enone Ketone → Ketal Luche reduction Enone → Allyl-OH Ketone → Ketal O-H → O-MOM Dehydration → Diene Aldehyde → Alkyl-OH Alkyl-OH → Aldehyde Barton-McCombie reduction Allyl-OR → Allyl-H Wittig-methyl CompE+-Aldehyde/CarboxEster+Wittig ConjReduct-Acylation Enone ConjReduct CarboxEster enolate+Enal Enal+Enolate ConjReduct-Alkylation CarboxEster enolate+Alkyl-X EnoateEster ConjReduct Alkyl-X+Enolate Claisen acylation, Mander Ketone enolate+Mander Hydrosulfidation Alkyne Li-Alkynyl+Ketone Li/H → Li-Alkynyl Allyl-X → Allyl-H Mechanism KetoEster → Ester Diels-Alder, Enal Robinson annulation, diketone Ketone enolate+Enone |
Reagents: | Acrolein LiNiPr2 CrO3, H2SO4 (Jones) Glycol BH4-Na+, CeCl3 CS2 HSnBu3 Li°/NH3 MeI Glycol Li°/NH3 O=C(OR)CN Cl-CH2-OR Li°/NH3 MeI Alkynyl-Li Thiol, phenyl POCl3 BH4-Na+ RaNi Dess-Martin PPh3=CH2 Bromide, lithium AIBN AIBN Wieland-Miescher Methacrolein SnCl4 Fluoride, potassium |