Total synthesis of Bourbonene:
| Reference: | White, J. D.; Gupta, D. N. J. J. Am. Chem. Soc. 1966, 88, 5364-5365. DOI |
| Reactions: | Ketone azaenolate+Alkyl-X • Alkyl-X+Azaenolate • Ketone → Imine • Claisen acylation, formate • Ketone enolate+Formate • KetoAldehyde → Allyl-OH • Allyl-X → Allyl-H • Photochemistry 2+2 • Cyclobutane • Bicyclo(320) • Wittig-methyl • Alkene isomerization • Allyl-OH → Allyl-Cl • |
| Reagents: | Alkyl-MgX • NaOMe • Formate, ethyl • AlH4-Li+ • SOCl2 • Allyl-Cl • AlH4-Li+ • Photochemistry • PPh3=CH2 • HCl, EtOH • |