Total synthesis of Zizaene (Coates):
| Reference: | Coates, R. M.; Sowerby, R. L. J. Am. Chem. Soc. 1972, 94, 5386. DOI |
| Reactions: | Ketone+Mg-Alkyl • Mg-Alkyl+Ketone • Wagner-Meerwein • Alkene → Bromohydrin • Ketone-α-Halo → Enone • ConjAdd Cu-Me • Cu-Me+Enone • CompE+-Ketone/CarboxEster+M-R • Wolff-Kishner • Ketone → CH2 • N-C(O)R → N-CH2R • 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 • Cyclopentane • Bicyclo(321) • Benzylic oxidation → Benzyl-Br • Wohl-Ziegler bromination • Dehydrohalogenation → Ene • Ozonolysis Ph • CarboxAcid → CarboxAmide • Claisen acylation, formate • Ketone enolate+Formate • Alkyl-OH → Ketone-α-Halo • O-H → O-C(O)R • N-H → N-C(O)R • Alkyl-OH → Ketone • |
| Reagents: | Alkyl-MgX • Acetic acid • Carbonate, calcium • Bromoacetamide-N • HClO4 • CrO3, H2SO4 (Jones) • Carbonate, calcium • Me-Cuprate • Hydroxide, potassium • Acetic anhydride • O3 • 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) • NBS • |