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Author Egan, Richard S. ♦ Martin, Jerry R. ♦ Mcalpine, James B. ♦ Kurath, Paul ♦ Stanaszek, Ruth S. ♦ Goldstein, Alma W. ♦ Johnson, Leroy F.
Source J-STAGE
Content type Text
Publisher JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
Language English
Abstract $^{13}C-NMR$ studies have confirmed the structures of (8S)-8-hydroxyerythromycins A- and B-6, 9;9, 11-acetal proposed by KROWICKI and $ZAMOJSKI^{2,$ 3)} for the products of the m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycins A- and B-6, 9-hemiacetal. The preparations of (8S)-8-methylthiomethoxy- and (8S)-8-methoxyerythromycin B-6, 9;9, 11-acetals are described. The latter are stable in aqueous acetic acid under conditions which convert (8S)-8-hydroxyerythromycin B-6, 9;9, 11-acetalinto (8S)-8-hydroxyerythromycin B. In a paper describing the preparation of the $C_{8}-epimeric$ 8-hydroxyerythromycins B, we $reported^{1)}$ that buffered m-chloroperbenzoic acid oxidation of 8, 9-anhydroerythromycin B-6, 9-hemiacetal (1), followed by catalytic reduction of the resulting N-oxide to the free amine, gave (8S, 9S)-8, 9-anhydroerythromycin B-6, 9-hemiacetal-8, 9-epoxide (2). Our assignment of structure 2 was based on the expected course of olefin epoxidation with peracids and with apparently compatible spectral properties. In addition, the facile conversion of 2 to (8S)-8-hydroxyerythromycin B (3) in aqueous acetic acid was expected for the strained epoxy spiroacetal structure (2).
ISSN 00218820
Learning Resource Type Article
Publisher Date 1978-01-01
e-ISSN 18811469
Journal The Journal of Antibiotics(antibiotics1968)
Volume Number 31
Issue Number 1
Page Count 8
Starting Page 55
Ending Page 62


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