Total synthesis of Zizaene (Piers):
| Reference: | Piers, E.; Banville, J. Chem. Commun. 1979, 1138. DOI |
| Reactions: | Sulfide → Sulfoxide • Cu-Vinyl+Enone • ConjAdd Cu-Vinyl • Sulfoxide-Ei → Enone • Ketone → Enone • Hydroboration → Alkyl-OH • 1,3-Sigmatropic • Cyclopentene • Bicyclo(430) • Li-Sulfone+Alkyl-X • Alkyl-X+Li-R • Cyclopentane • Bicyclo(321) • Spiro(44) • Ketone → Ketone-α-SR • Alkyl-SO2R → Alkyl-H • Sulfide → Sulfone • Ketal → Ketone • ConjAdd M-SR • Enone+Thiolate • Ketone → Ketal • O-H → O-SO2Ar • |
| Reagents: | Vinyl-Cu • LiNiPr2, HMPA • Disulfide, phenyl • Periodate, sodium • Thiol, phenyl • BH3·SMe2 • H2O2, NaOH • TsCl, Py • Na(Hg) • Oxalic acid • KOtBu • HMPA (solvent) • Glycol • Perbenzoic acid, 3-chloro • |