SYNTHETIC STUDIES OF ERYTHROMYCIN DERIVATIVES SYNTHESES AND ANTIMICROBIAL ACTIVITIES OF 3''-<i>EPI</i>-ERYTHROMYCIN A AND (9<i>S</i>)11-DEHYDROXY-9-DEOXO-9-HYDROXY-11-OXOERYTHROMYCIN A

MASAYA NAKATA; TETSURO TAMAI; YUKIKO MIURA; MITSUHIRO KINOSHITA; KUNIAKI TATSUTA

doi:10.7164/antibiotics.46.813

SYNTHETIC STUDIES OF ERYTHROMYCIN DERIVATIVES

SYNTHESES AND ANTIMICROBIAL ACTIVITIES OF 3''-EPI-ERYTHROMYCIN A AND (9S)11-DEHYDROXY-9-DEOXO-9-HYDROXY-11-OXOERYTHROMYCIN A

MASAYA NAKATA, TETSURO TAMAI, YUKIKO MIURA, MITSUHIRO KINOSHITA, KUNIAKI TATSUTA

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JOURNAL FREE ACCESS

1993 Volume 46 Issue 5 Pages 813-826

DOI https://doi.org/10.7164/antibiotics.46.813

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Abstract

Two new derivatives, 3''-epi-erythromycin A (2) and (9S)-11-dehydroxy-9-deoxo-9-hydroxy-11-oxoerythromycin A (3), have been synthesized by using glycosylation with glycal (Ferrier rearrangement), bromomethoxylation and bis(tributyltin) oxide-bromine oxidation as the key steps. Their antimicrobial activities were compared with those of erythromycin A (1).

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