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Total synthesis of Zizaene New:
Reference: Coates, R. M.; Sowerby, R. L. J. Am. Chem. Soc. 1972, 94, 5386. DOI
Keywords: Dehydrohalogenation -> Ene • Alkyl-OH -> Ketone-α-Halo • Ozonolysis Ph • CarboxAcid -> CarboxAmide • N-H -> N-C(O)R • Alkyl-OH -> Ketone • Claisen acylation, formate • Ketone enolate+Formate • Ketone+Mg-Alkyl • Wagner-Meerwein • Allylic oxidation -> Allyl-Br • Bromohydrin • Ketone-α-Halo -> Enone • ConjAdd Cu-R • Cu-Me+Enone • Wolff-Kishner • Ketone -> CH2 • CarboxAmide -> Amine • Enol -> Enesulfide • Ketone enolate+Me-I • Ketone epimerization • Li-Sulfide+Ketone • Reductive elimination - S/OR • N-H -> N-NO • Diazoalkane • Nitrosoamide -> Diazo • Tiffeneau-Demjanov rearrangement •
Reagents: Alkyl-MgX • Acetic acid • NBS • Carbonate, calcium • Bromoacetamide-N • HClO4 • CrO3, H2SO4 (Jones) • Carbonate, calcium • LiCuMe2 • Hydroxide, potassium • Acetic anhydride • O3 • Oxalyl chloride • NH3 • AlH4-Li+ • Acetic anhydride • CrO3·Py2 (Collins) • NaH • Formate, ethyl • TsOH • Li°/NH3 • MeI • NaOMe • Benzoyl chloride • Li°/NH3 • NaOMe •

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