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Total synthesis of Defucogilvocarcin M:
Reference: Takemura, I.; Imura, K.; Matsumoto, T.; Suzuki, K. Org. Let. 2004, 6, 2503. DOI
Keywords: Li/I -> Li-Aryl • O-SiMe2tBu -> O-H • Ketone -> Ketal(Me) • Alkyl-OH -> Ketone-α-OR • Aldehyde -> Acetal • CarboxEster -> Alkyl-OH • Benzyl-OH -> Aldehyde • O-H -> O-C(O)R • Acetal -> Aldehyde • Pinnick oxidation • Aldehyde -> CarboxAcid • O-Bn -> O-H • Benzyne Cycloaddition • Cyclobutane • Electrocyclic-4π • Li/Br -> Li-Vinyl • Li-Vinyl+Ketone • Pd-Sonogashira • Si-Alkynyl -> H-Alkynyl • Electrocyclic-6π • Naphthalene synthesis • Alkyne -> Vinyl-Br •
Reagents: BuLi(n) • HF • TsOH • DMSO, Py·SO3 • Alkynyl-SiR3 • Carbonate, potassium • AlH4-Li+ • MnO2 • Vinyl-Li • BuLi(tert) • DMAP • Acetic acid • Chlorite, sodium • H2, Pd • PdCl2(PPh3)2

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