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Total synthesis of Erythromycin A:
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
Keywords: Diol-1,2 → Ketal • Alkyl-OH → Ketone-α-OR • Alkene cleavage • Ozonolysis • Alkyl-OH → Ketone-1,3-di • ConjAdd M-SR • Ketone → Alkyl-OH • O-H → O-C(O)R • Alkene cleavage • Ozonolysis • Alkyl-X → Alkyl-SR • Dehydration → Enone • Alkene → Diol-1,2 • Alkyl-SR → Alkyl-H • O-Bn → O-H • Selenoxide-Ei → Ene • Aldol-Li → Aldol • Ketone → EnolCarboxylate • O-H → O-SO2R • Enone → Allyl-OH • CarboxEster(thio) enolate+Aldehyde • CarboxEster epimerization • CarboxEster(thio) → Lactone • Alkyl-OH → Alkyl-SeR • Alkyl-OH → Alkyl-SeR • Lactone-9+ • Aldol-enamine → Aldol •
Reagents: NaH • Sulfonyl chloride, methane • Acetic acid • OsO4 • Bisulfate, sodium • Me2C(OMe)2 • Acetic acid, trifluoro • NEtiPr2 • RaNi • Selenocyanate, o-nitrophenyl • H2O2 • Me2S • Mesityl-Li • Acetic anhydride, trifluoro • NEtiPr2 • KH • BH4-Na+ • Acetyl chloride • DMAP • Thiol, Benzyl • BuLi(n) • AlH4-Li+ • DMAP • RaNi • Selenocyanate, o-nitrophenyl • H2O2 • Me2S • LiNiPr2 • BuLi(tert) • Sulfonyl chloride, methane • PBu3 • Proline •

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