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Total synthesis of Bulnesene, α:
Reference: Ratcliffe, R.; Heathcock, C. H. J. Am. Chem. Soc. 1971, 93, 1746. DOI
Keywords: O-H → O-C(O)R • Ketone → Ketal • O-C(O)R → O-H • O-H → O-Bn • Alkyl-OH → Ketone • Hydroboration alkene • Alkyl-OH → Ketone • O-Bn → O-H • O-H → O-SO2R • Hydroboration alkene • Ketone epimerization • Wittig-alkyl+Ketone • Wittig-methyl • Hydrogenation Alkene • CompRed-Alkene/Ketone+H2 • Ketone epimerization • Li-Me+Ketone • Ketone+Li-Alkyl • Wagner-Meerwein • Wagner-Meerwein •
Reagents: Acetic anhydride, Py • Glycol • AlH4-Li+ • NaH • Benzyl-X • BH3 • H2O2, NaOH • CrO3·Py2 (Collins) • NaOMe • PPh3=CH2 • Acetic acid • Al2O3 • PPh3=CH-Me • BH3 • H2O2, NaOH • CrO3·Py2 (Collins) • H2, Pd • TsCl, Py • H2, Pd • TsCl, Py • Acetic acid • MeLi • Wieland-Miescher • Acetic acid •

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