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Total synthesis of Vernolepin Analog:
Reference: Marshall, J. A.; Flynn, G. A. J. Org. Chem. 1979, 44, 1391. DOI
Keywords: Ketone → Alkyl-OH • CarboxEster → Alkyl-OH • Alkyl-OH → Alkyl-SeR • O-SiMe2tBu → O-H • Lactone-5 • Claisen acylation, carbonate • Ketone enolate+Carbonate • Ketoester enolate+Alkyl-X • Alkyl-X+Enolate • Selenoxide-Ei → Ene • Lactone enolate+Iminium • Iminium+Enolate • Ozonolysis • O-H → O-SiMe2tBu • Ketone enamine+Alkyl-X • Alkyl-X+Enamine • Allyl-X → Allyl-I • Finkelstein reaction •
Reagents: AlH4-Li+ • SiMe2tBu-Cl • O=C(OR)2 • NaH • NaH • Iodoacetate • AlH4-Li+ • O3 • Me2S • Selenocyanate, o-nitrophenyl • PBu3 • H2O2 • Fluoride, R4N+ • LiNiPr2 • CH2=NMe2+I- • Imidazole • Allyl-Cl • Iodide, sodium • NEtiPr2

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