Total synthesis of Moenicol:
| Reference: | Grieco, P. A.; Masaki, Y.; Boxler, D. J. Am. Chem. Soc. 1975, 97, 1597. DOI |
| Reactions: | O-Bn → O-H • Li-Vinyl+Aldehyde • Aldehyde+Li-Vinyl • Ozonolysis • CompOx-Alkene/Alkene+O3 • Claisen-EnolEther • HWE → EnoateEster • EnoateEster enolate+Alkyl-X • Allyl-X+Enolate • Selenoxide-Ei → Ene • EnoateEster ConjReduct • CarboxEster → Alkyl-OH • O-H → O-SO2Me • Alkyl-X → Alkyl-SeR • Selenolate+Alkyl-X • CarboxEster → CarboxAcid • CarboxAcid → CarboxEster • O-THP → O-H • O-H → O-THP • |
| Reagents: | O3 • Zn° • Vinyl-Li • Vinyl-OR • P(O)(OR)2CH2-C(O)OR' • Hydroxide, potassium • Li°/EtNH2 • Diazomethane • LiNiPr2 • Allyl-Br • AlH4-Li+ • H2O2 • Sulfonyl chloride, methane, Py • Selenolate, o-nitrophenyl • TsOH • DHP • |