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 |
| Reactions: | O-H → O-SO2Me • Alkyl-X → Alkyl-Br • 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-Me • Cyclohexane • Bicyclo(440) • CompE+-Enone/Alkyl-X+Cu-R • Ketone enolate+Alkyl-X (intram) • Alkyl-X+Enolate (intram) • Alkyl-OH → Alkyl-Br • |
| Reagents: | TsOH • Alkyl-MgX • H2SO4 • Sulfonyl chloride, methane, Py • Bromide, lithium • Thiol, (CH2)2-SH • BF3·OEt2 • RaNi • Me-Cuprate • HMPA (solvent) • |