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Total synthesis of Zizaene:
Reference: Coates, R. M.; Sowerby, R. L. J. Am. Chem. Soc. 1972, 94, 5386. DOI
Keywords: Benzyl-H → Benzyl-Br • 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 • Mg-Alkyl+Ketone • Wagner-Meerwein • Alkene → 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 • Oxalyl chloride • AlH4-Li+ • Acetic anhydride • CrO3·Py2 (Collins) • NaH • Formate, ethyl • TsOH • Li°/NH3 • MeI • NaOMe • Alkyl-Li • Benzoyl chloride • Li°/NH3 • NaOMe • CrO3, H2SO4 (Jones) •

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