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Issue 4, 2015
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Synthesis of 17-membered azalides from a 16-membered macrolide utilizing amide-selective silane reduction

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Abstract

The synthesis of 17-membered azalides was achieved using the following key steps: (i) Beckmann rearrangement of 16-membered oxime derivatives obtained from 3,4′-dideoxymycaminosyltylonolide (DDMT), (ii) amide-selective silane reduction of the corresponding ring-enlarged lactams catalyzed by RhCl3 in the presence of Et3N, and (iii) N-methylation of the resulting secondary amines.

Graphical abstract: Synthesis of 17-membered azalides from a 16-membered macrolide utilizing amide-selective silane reduction

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Publication details

The article was received on 29 Oct 2014, accepted on 02 Dec 2014 and first published on 02 Dec 2014


Article type: Concise Article
DOI: 10.1039/C4MD00489B
Med. Chem. Commun., 2015,6, 581-585

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    Synthesis of 17-membered azalides from a 16-membered macrolide utilizing amide-selective silane reduction

    A. Seki, T. Mori, K. Sasaki, Y. Takahashi, T. Miyake and Y. Akamatsu, Med. Chem. Commun., 2015, 6, 581
    DOI: 10.1039/C4MD00489B

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