Synthesis of 2‘-O-Benzoyl-3-keto-6-O-propargyl-11,12-carbamoyl Erythromycin A

Autor: Kerdesky, F. A. J., Premchandran, R., Wayne, G. S., Chang, S.-J., Pease, J. P., Bhagavatula, L., Lallaman, J. E., Arnold, W. H., Morton, H. E., King, S. A.
Zdroj: Organic Process Research & Development; November 2002, Vol. 6 Issue: 6 p869-875, 7p
Abstrakt: An efficient and practical synthesis of 2‘-O-benzoyl-3-keto-6-O-propargyl-11,12-carbamoyl erythromycin A (4) is described. The semisynthetic macrolide was prepared on large scale in seven steps in 38% overall isolated yield from the readily available bis(trimethylsilyloxy) ether of erythromycin A oxime ketal (5). The chemistry, which required no chromatography, involved selective hydrolysis, alkylation, and hydroxyl protection transformations.
Databáze: Supplemental Index