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Total synthesis of Culmorin:
Reference: Roberts, B. W., Poonian, M. S.; Welch, S. C. J. Am. Chem. Soc. 1969, 91, 3400-3500. DOI
Keywords: Dieckmann • CarboxEster enolate+CarboxEster • Cyclopentanone • Alkene cleavage • Claisen acylation, ester • Ketone enolate+CarboxEster • Cyclopentanone • Li-Me+Ketone • Ketone+Li-Alkyl • CompE+-Ketone/Ketone+M-R • Dehydration → Ene • Ketone enolate+Alkyl-X • Alkyl-X+Enolate • Hydroboration alkene • Alkyl-OH → CarboxAcid • Decarboxylation β-keto acid • CarboxAcid → CarboxEster • Ketone → Alkyl-OH • Ketone enolate+Alkyl-X • CarboxEster → Alkyl-OH •
Reagents: NaH • Allyl-Cl • Permanganate, potassium • Periodate, sodium • HCl, MeOH • NaH • MeLi • SOCl2 • Pyridine • NaH • Bromoacetate • RuO4 • Periodate, sodium • Diazomethane • NaOEt • HCl •

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