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Total synthesis of Erythromycin A (Part 1):
| Reference: | Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E; Au-Yeung, B. W.; Balaram,P.; Browne,L. J.; Card, P. J.; Chen, C. H. et. al J. Am. Chem. Soc. 1981, 103, 3210. DOI (Part 2) |
| Reactions: | Alkyl-X → Alkyl-SR • Dehydration → Enone • Alkene → Diol-1,2 • CompOx-Alkyl-OH/Sulfide+OsO4 • Alkyl-SR → Alkyl-H • O-Bn → O-H • Selenoxide-Ei → Ene • Aldol-Li → Aldol • Ketone enolate+Aldehyde • Ketone → EnolCarboxylate • Enone → Allyl-OH • Aldol-enamine → Aldol • Bicyclo(440)-thia • Ozonolysis • Acetal → Aldehyde • Alkyl-OH → Ketone-α-OR • Enone → Allyl-OH • Diol-1,2 → Ketal • Alkyl-X → Alkyl-SeR • Selenide → Selenoxide • O-MOM → O-H • Diol-1,2 → Ketone-α-OR • CompOx-Alkyl-OH/Sulfide+DMSO • Alkyl-OH → Ketone-1,3-di • O-H → O-SO2Me • Selenoxide-Ei → Ene • Alkyl-X → Alkyl-SeR • Dehydrosulfonoxylation → Enone • Ketone → Alkyl-OH • ConjAdd M-SR • Enone+Thiolate • Ketone → Alkyl-OH • O-H → O-C(O)R • Alkyl-SR → Alkyl-H • O-Bn → O-H • Alkyl-OH → Alkyl-SeR • Selenide → Selenoxide • Selenoxide-Ei → Ene • Ozonolysis • O-Bn → O-H • |
| Reagents: | NaH • Sulfonyl chloride, methane, Py • Acetic acid • OsO4 • Bisulfate, sodium • Me2C(OMe)2 • Acetic acid, trifluoro • DMSO, (CF3CO)2O • O3; Me2S • RaNi • Selenocyanate, o-nitrophenyl • H2O2 • Mesityl-Li • DMSO, (CF3CO)2O • NEtiPr2 • KH • BH4-Na+ • Acetyl chloride • Sulfonyl chloride, methane, Py • PBu3 • Proline • HMPA (solvent) • BH4-Na+ • KH • TsOH • NEtiPr2 • DMAP • BuLi(n) • AlH4-Li+ • Acetic anhydride, DMAP • RaNi • Selenocyanate, o-nitrophenyl • H2O2 • PBu3 • DMF (solvent) • O3; Me2S • Bicarbonate, sodium • |