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Total synthesis of Pentalenene (Mehta):
Reference: Mehta, G.; Rao, K. S. J. Am. Chem. Soc. 1990, 108, 8015. DOI
Keywords: Alkyl-OH → Ketone • Hydroboration → Alkyl-OH • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Wacker oxidation • Alkene → Ketone • Aldol-Na → Enone • Cyclopentenone • Ketone epimerization • Cationic cyclization • Mechanism • Cyclopentane • Wittig-methoxymethyl • EnolEther → Aldehyde • Aldehyde enolate+Alkyl-X • Alkyl-X+Enolate • Wolff-Kishner • Aldehyde → CH3
Reagents: BH-BBN • H2O2 • 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 •

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