Total synthesis of Culmorin:
| Reference: | Roberts, B. W., Poonian, M. S.; Welch, S. C. J. Am. Chem. Soc. 1969, 91, 3400-3500. DOI |
| Reactions: | Dieckmann • CarboxEster enolate+CarboxEster • Cyclopentanone • Alkene cleavage • Claisen acylation, ester • Ketone enolate+CarboxEster • Cyclopentanone • Bicyclo(421) • Li-Me+Ketone • Ketone+Li-Alkyl • CompE+-Ketone/Ketone+M-R • Dehydration → Ene • Ketone → C=CH2 • Ketone enolate+Alkyl-X • Bromoacetate+Enolate • Hydroboration → Alkyl-OH • Alkyl-OH → CarboxAcid • Decarboxylation β-keto acid • CarboxAcid → CarboxEster • Ketone → Alkyl-OH • Ketone enolate+Alkyl-X • CarboxEster → Alkyl-OH • CarboxEster → CarboxAcid • |
| Reagents: | NaH • Allyl-Cl • Permanganate, potassium • Periodate, sodium • NaH • Me-Li • SOCl2 • Pyridine • NaH • Bromoacetate • RuO4 • Periodate, sodium • Diazomethane • NaOEt • HCl, H2O • HOMe (react) • Acetic acid • |