Total synthesis of Clovene (Funk):
| Reference: | Funk, R. L.; Novak, PM.; Abelman, M. M Tetrahedron Lett. 1988, 29, 1493. DOI |
| Reactions: | Peterson → EneSulfide • Li-Silane+Ketone • Shapiro reaction • Ketone → Alkene • Cu-Me+Enone • ConjAdd Cu-Me • 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 • Cyclopentanone • Bicyclo(430) • Ketene Cycloaddition • Cyclobutane • Bicyclo(331) • Bicyclo(420) • CarboxAcid → Ketene • Ketene synthesis • Ketone → Hydrazone • Ketene acetal(thio) → CarboxAcid • Ketal(thio) → CH2 • |
| Reagents: | Alkyl-MgX • Me-Cuprate • HgCl2 • NaH • RaNi • Hydrazine, tosyl • BuLi(n) • Pyridinium, 2-halo • NEt3 • LiC(SR)3 • MeI • |