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Total synthesis of Valerane:
Reference: Posner, G. H.; Sterling, J. J.; Whitten, C. E.; Brunelle, D. J. J. Am. Chem. Soc. 1975, 97, 107. DOI
Keywords: O-H → O-SO2R • Finkelstein reaction • Mg-Alkyl+Ketone • Enone-β-OR+Mg-R • Enone-β-OR → Enone • Stork-Danheiser • Ketone → EnolEther • Ketone → Ketal(thio) • Ketal(thio) → CH2 • Ketone → CH2 • ConjAdd-Alkylation • Cu-Me+Enone • ConjAdd Cu-R • Ketone enolate+Alkyl-X, Intram • Alkyl-X+Enolate •
Reagents: TsOH • Alkyl-MgX • H2SO4 • Sulfonyl chloride, methane • Bromide, lithium • Thiol, (CH2)2-SH • BF3·OEt2 • RaNi • LiCuMe2 • HMPA (solvent) •

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