Total synthesis of Bulnesene, α:
| Reference: | Ratcliffe, R.; Heathcock, C. H. J. Am. Chem. Soc. 1971, 93, 1746. DOI |
| Reactions: | O-C(O)R → O-H • O-Bn → O-H • O-Bn → O-H • Hydroboration → Alkyl-OH • Ketone epimerization • Wittig-alkyl+Ketone • Wittig-methyl • Hydrogenation Alkene • CompRed-Alkene/Ketone+H2 • Ketone epimerization • Li-Me+Ketone • Ketone+Li-Alkyl • Wagner-Meerwein • Cycloheptane • Cyclopentane • Wagner-Meerwein • Bicyclo(530) • Ketal → Ketone • Wittig-methyl • O-H → O-SO2Ar • O-H → O-C(O)R • Ketone → Ketal • O-H → O-Bn • Alkyl-OH → Ketone • O-H → O-SO2Ar • Hydroboration → Alkyl-OH • Alkyl-OH → Ketone • |
| Reagents: | Acetic anhydride, Py • Glycol • AlH4-Li+ • NaH • Benzyl-X • H2O2, NaOH • CrO3·Py2 (Collins) • NaOMe • PPh3=CH2 • Acetic acid • Al2O3 • PPh3=CH-Me • BH3 • H2O2, NaOH • CrO3·Py2 (Collins) • HCl, MeOH • H2, Pd • TsCl, Py • H2, Pd • PPh3=CH2 • TsCl, Py • Acetic acid • Me-Li • Wieland-Miescher • Acetic acid • |