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Total synthesis of Hirsutene:
Reference: Krische, M. J.; Wang, J.-C. Angew. Chem IE. 2003, 42, 5855. DOI
Keywords: O-H -> O-SO2R • CarboxEster -> Alkyl-OH • Alkyl-OH -> Aldehyde • HWE -> Enone • CompE+-Aldehyde/CarboxEster+Phosphonate • Li-Alkynyl+Chlorocarbonate • Li/H -> Li-Alkynyl • Li-Alkynyl+Alkyl-X • Aldol-Na -> Enone • Ozonolysis • CompOx-Alkene/Alkyne+O3 • Mechanism • Cycloaddition Allyl anion •
Reagents: TsCl, Py • Alkynyl-Li • MeLi • O=C(OR)Cl • O3 • P(O)(OR)2CHMe-C(O)R • NaH • H2, Pd • AlH4-Li+ • DMSO, (COCl)2 • NH3 • DMSO (solvent) • PBu3

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