| Reference: | Taschner, M. J.; Shahripour, A. J. Am. Chem. Soc. 1985, 107, 5570. DOI |
| Keywords: | CarboxEster -> CarboxAcid CarboxEster -> Alkyl-OH Alkyl-OH -> Aldehyde Wittig-methoxymethyl Reductive formylation Alkene cleavage Haloform Ketone -> Alkyl-OH Lactone-5 Lemieux-Johnson oxidation Alkene cleavage Bredt's Rule ConjReduct-Alkylation Ketone enolate+Alkyl-X Bromoacetate+Enolate Enone ConjReduct Lactone enolate+Alkyl-X Lactone-5 Lactone enolate+Alkyl-X Mg-Alkyl+Ketone Alkyl-OH -> Ketone Aldol-H+ -> Aldol Dehydration -> Ene Lemieux-Johnson oxidation CompE+-Aldehyde/Ketone+Wittig CompRed-Ketone/CarboxEster+B-H Lactone-5 |
| Reagents: | Li°/NH3 Bromoacetate Hydroxide, potassium Li°/NH3 LiNiPr2 AlH4-Li+ DMSO, (COCl)2 NEt3 PPh3=CH-OMe HCl, H2O MeMgBr OsO4, NaIO4 SOCl2 BH3CN-Na+ Acetic acid LiNiPr2, HMPA Allyl-Br OsO4, NaIO4 Hypochlorite, potassium DMSO, (COCl)2 MeI |