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

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