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Total synthesis of Longifolene (Schultz):
Reference: Schultz, A. G.; Puig, S. J. Org. Chem. 1985, 50, 915-916. DOI
Keywords: N-H → N-C(O)R • Cycloaddition Diazoalkane • Cyclopropane • Cycloheptane • Azo fragmentation • 1,3-Sigmatropic • Bicyclo(221) • Birch alkylation • CarboxAmide enolate+Alkyl-X • Alkyl-X+Enolate • EnolEther → Ketone • Acetal → Aldehyde • Acyl shift • Bromoetherification • Dehydrohalogenation → Diene • Decarboxylation β-keto acid • Ketone → Hydrazone • Hydrogenation Alkene • Aldehyde → Acetal • CarboxEster → CarboxEster • Ketone+Li-Alkyl • Li-Me+Ketone • Dehydration → Ene • CarboxEster → CarboxAcid • Ketal → Ketone •
Reagents: Na°/NH3 • HCl, MeOH • O=C(OR)Cl • Bicarbonate, sodium • Orthoformate • HCl, MeOH • NaOMe • DBN • TsOH • Aziridine • H2, Pd • Hydroxide, potassium • MeLi • SOCl2 • LiNiPr2 • MeI • Bromoacetamide-N •

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