Total synthesis of Pentalenene (Mehta):
| Reference: | Mehta, G.; Rao, K. S. J. Am. Chem. Soc. 1986, 108, 8015. DOI |
| Reactions: | Alkyl-OH → Ketone • Hydroboration → Alkyl-OH • Ketone enolate+Alkyl-X • Allyl-X+Enolate • Wacker oxidation • Alkene → Ketone • Aldol-Na → Enone • Cyclopentenone • Bicyclo(630) • Ketone epimerization • Cationic cyclization • Mechanism • Cyclopentane • Bicyclo(330) • Wittig-methoxymethyl • EnolEther → Aldehyde • Aldehyde enolate+Alkyl-X • Alkyl-X+Enolate • Wolff-Kishner • Aldehyde → CH3 • |
| Reagents: | BH-BBN • H2O2, NaOH • CrO3Cl·PyH (PCC) • LiN(SiMe3)2 • Allyl-Br • Hydroxide, potassium • NaH • PdCl2 • CuCl • O2 • BF3·OEt2 • Formic acid • PPh3=CH-OR • NaOtBu • HClO4 • KH • MeI • Hydrazine • Glycol • |