Total synthesis of Rimuene New:
| Reference: | Ireland, R. E.; Mander, L. N. J. Org. Chem. 1967, 32, 689-696. DOI |
| Reactions: | Birch reduction • Enone → Ketone • Enone enolate+Alkyl-X • Deconjugative alkylation • Alkyl-X+Enolate • O-H → O-C(O)R • Wolff-Kishner • Ketone → CH2 • Alkyl-OH → Ketone • Wittig-methoxymethyl • EnolEther → Aldehyde • Aldehyde enolate+Alkyl-X • Alkyl-X+Enolate • Wittig-methyl • |
| Reagents: | Li°/NH3 • KOtBu • MeI • Benzoyl chloride • Pyridine • Hydrazine • PPh3=CH-OR • HClO4 • CrO3 • KOtBu • MeI • PPh3=CH2 • Acetone (solvent) • |