Total synthesis of Jasmone, cis- (McMurry):
| Reference: | McMurry, J. E.; Melton, J. J. Am. Chem. Soc. 1971, 93, 5309. DOI |
| Reactions: | Nef reaction • Alkyl-NO2 → Ketone • Nitronate+Enone • ConjAdd Nitronate • Aldol-Na → Enone • Cyclopentenone • Alkyne → Ene-cis (Lindlar) • CompRed-Alkyne/Alkene+H2 • Alkyl-X → Alkyl-NO2 • |
| Reagents: | Methyl vinyl ketone • NHiPr2 • Nitrite, sodium • TiCl3 • Hydroxide, sodium • H2, Pd • DMSO (solvent) • |