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Total synthesis of Moenicol:
Reference: Grieco, P. A.; Masaki, Y.; Boxler, D. J. Am. Chem. Soc. 1975, 97, 1597. DOI
Keywords: CarboxEster → CarboxAcid • O-Bn → O-H • EnoateEster ConjReduct • CarboxAcid → CarboxEster • O-H → O-THP • CarboxEster → Alkyl-OH • Li-Vinyl+Aldehyde • Ozonolysis • CompOx-Alkene/Alkene+O3 • Claisen-Enol ether • HWE → EnoateEster • EnoateEster enolate+Alkyl-X • Alkyl-X+Enolate • O-H → O-SO2R • Alkyl-X → Alkyl-SeR • Selenoxide-Ei → Ene •
Reagents: O3 • Zn° • Vinyl-Li • Vinyl-OR • P(O)(OR)2CH2-CO2R • Hydroxide, potassium • Li°/EtNH2 • Diazomethane • DHP • LiNiPr2 • Allyl-Br • AlH4-Li+ • H2O2 • Sulfonyl chloride, methane • Selenolate, o-nitrophenyl •

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