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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 • Alkyl-X+Li-R • 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)2CHR-C(O)R' • NaH • H2, Pd • AlH4-Li+ • DMSO, (COCl)2 (Swern) • NH3 • DMSO (solvent) • PBu3

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