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Total synthesis of Erythromycin A (Part 2):
| 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 1) |
| Reactions: | CarboxEster(thio) enolate+Aldehyde • CarboxEster epimerization • CarboxEster(thio) → Lactone • Lactone-9+ • CompNu-O-H/O-H+RC(O)X • CarboxEster(thio) → CarboxEster • O-H → O-C(O)R • O-C(O)R → O-H • O-H → O-SO2Me • Alkyl-X → Alkyl-N3 • Azide → Amine • N-H → N-C(O)OR • CompNu-Amine/Alkyl-OH+RC(O)X • Ketal → Diol-1,2 • O-H → O-C(O)NR2 • CarboxEster → CarboxEster(thio) • CarboxEster(thio) → CarboxEster(thio) • |
| Reagents: | LiNiPr2 • BuLi(tert) • Carbonate, sodium • DMAP • Sulfonyl chloride, methane • Hydroxide, lithium • Azide, sodium • HMPA (solvent) • H2, Pt • O=C(OR)Cl • NH2OH • NEt3 • O=C(SR)Cl • Acetic acid, trifluoro • NEt3 • Acetic acid • |