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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 (phenol) • Acetal → Aldehyde • Pinnick oxidation • Aldehyde → CarboxAcid • O-Bn → O-H (phenol) • 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 • Mechanism •
Reagents: BuLi(n) • HF • TsOH • DMSO, Py·SO3 (Parikh-Doering) • 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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