Total synthesis of Longifolene (Schultz):
| Reference: | Schultz, A. G.; Puig, S. J. Org. Chem. 1985, 50, 915-916. DOI |
| Reactions: | N-H → N-C(O)R • Cycloaddition Diazoalkane • Bicyclo(540) • Cyclopropane • Cycloheptane • Azo fragmentation • Bicyclo(410) • 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 • Aldehyde → Hydrazone • Hydrogenation Alkene • Aldehyde → Acetal(Me) • CarboxEster → CarboxEster • Ketone+Li-Alkyl • Li-Me+Ketone • Dehydration → Ene • Ketone → C=CH2 • CarboxEster → CarboxAcid • Ketal → Ketone • |
| Reagents: | Na°/NH3 • HCl, MeOH • O=C(OMe)Cl • Bicarbonate, sodium • Orthoformate • HCl, MeOH • NaOMe • HOMe (react) • DBN • TsOH • Aziridine • H2, Pd • Hydroxide, potassium • Me-Li • SOCl2 • LiNiPr2 • MeI • HOMe (react) • Bromoacetamide-N • |