Total synthesis of Bakkenolide-A (Evans):
| Reference: | Evans, D. A.; Sims, C. L.; Andrews, G. C. J. Am. Chem. Soc. 1977, 99, 5453. DOI |
| Reactions: | Enone enolate+Alkyl-X • Allyl-X+Enolate • Aldol-K → Enone • Cyclopentenone • Hydrogenation Enone • Bicyclo(430) • Li-Vinyl+Ketone • Enone+Li-R • Allyl-OH → Allyl-Br • Allyl-X → Allyl-SR • 2,3-Sigmatropic Anionic • Retro-Aldol • Alkene cleavage • Lemieux-Johnson oxidation • CarboxEster(dithio) → CarboxEster(thio) • Allylic oxidation → Allyl-OH • Lactone-5 • |
| Reagents: | KOtBu • Allyl-Cl • Hydroxide, potassium • OsO4, NaIO4 • KOtBu • H2, Pd • Propenyl-Li • PBr3 • Allyl-Br • NaH • HgCl2 • SeO2 • NaH • |