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Total synthesis of Clovene:
Reference: Funk, R. L.; Novak, PM.; Abelman, M. M Tetrahedron Lett. 1988, 29, 1493. DOI
Keywords: KeteneAcetal(thio) → CarboxAcid • Ketal(thio) → CH2 • Peterson → EneSulfide • Shapiro reaction • Ketone → Alkene • Cu-Me+Enone • ConjAdd Cu-R • Ketone enolate+Me-I • Mg-Alkyl+Ketone • Enone+Mg-R • Enone-β-OR → Enone • Stork-Danheiser • Li-Dithiane+Ketone • Ketone+Li-Sulfide • Reductive nucleophilic carboxylation • Li-Sulfide+Ketone • Pinacol, thio • Mechanism • Ketene Cycloaddition • Cyclobutane •
Reagents: Alkyl-MgX • LiCuMe2 • HgCl2 • MeI • RaNi • Hydrazine, tosyl • BuLi(n) • Pyridinium, 2-halo • NEt3 • LiC(SMe)3

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