Total synthesis of Cubane:
| Reference: | Eaton, P. E.; Cole, T. W. J. Am. Chem. Soc. 1964, 86, 3157. DOI |
| Reactions: | Ketone → Ketal • CarboxAcid → CarboxCl • CarboxCl → CarboxPerester • Cyclobutane • Allylic oxidation → Allyl-Br • Alkene → Dibromide-1,2 • Dehydrohalogenation → Enone • Diels-Alder, Enone • Bicyclo(221) • Photochemistry 2+2 • Cyclobutane • Favorskii • Cyclobutane • Decarboxylation • Mechanism • Favorskii • Ketal → Ketone • Ketal → Ketone • CarboxAcid → CarboxCl • CarboxCl → CarboxPerester • Decarboxylation • Cyclopentadienone • |
| Reagents: | Br2 • NHEt2 • Glycol • TsOH • HCl, H2O • Hydroxide, potassium • SOCl2 • Hydroperoxide, tbutyl • Cumene • H2SO4 • Hydroxide, potassium • SOCl2 • Hydroperoxide, tbutyl • NBS • |