Issue 4, 2015
From the journal:

MedChemComm

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

Atsushi Seki,*a   Toshihiro Mori,a   Kouji Sasaki,a   Yoshiaki Takahashi,a   Toshiaki Miyakea  and  Yuzuru Akamatsub  

* Corresponding authors

a Institute of Microbial Chemistry (BIKAKEN), Hiyoshi, 3-34-17 Ida, Nakahara-ku, Kawasaki-shi, Kanagawa 211-0035, Japan
E-mail: aseki@bikaken.or.jp
Fax: +81 44 755 3099

b Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan

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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Article information

DOI
https://doi.org/10.1039/C4MD00489B
Article type
Concise Article
Submitted
29 Oct 2014
Accepted
02 Dec 2014
First published
02 Dec 2014

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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