Total synthesis of Fichtelite:
| Reference: | Taber, D. F.; Saleh, S. A. J. Am. Chem. Soc. 1980, 102, 5085. DOI |
| Reactions: | Birch alkylation • CarboxAcid enolate+Alkyl-X • Alkyl-X+Enolate • Cu-Vinyl+Enone • ConjAdd Cu-Vinyl • Aldol-Li → Enone • Ketone enolate+Aldehyde • Cu-Me+Enone • ConjAdd Cu-Me • Mechanism • Hydrogenation alkene • Alkyl-OH → Alkyl-H(2°) • Diels-Alder, Intram, Ene • Cyclohexane • Bicyclo(440) • Ketone → Alkyl-OH • Sulfamic ester • Decarboxylation β-keto acid • EnolEther → Ketone • |
| Reagents: | Li°/NH3 • Propenyl-Li • CuBr·SMe2 • LiNiPr2 • Acetaldehyde • TsOH • Me-Cuprate • AlHiBu2 • SO2Cl2 • NHMe2 • Na°/NH3 • H2, Pt • Oxalic acid • |