Issue 3, 2012
From the journal:

Organic & Biomolecular Chemistry

A stereo-controlled access to functionalized macrolactams via an aza-Claisen rearrangement†

Young-Ger Suh,*a   Yong-Sil Lee,a   Seok-Ho Kim,a   Jae-Kyung Jung,b   Hwayoung Yun,a   Jaebong Jang,a   Nam-Jung Kima  and  Jong-Wha Jung*a  

* Corresponding authors

a College of Pharmacy, Seoul National University, Gwanakro 599, Gwanak-gu, Seoul, Korea
E-mail: ygsuh@snu.ac.kr
Fax: +82-2-888-0649
Tel: +82-2-880-7875

b College of Pharmacy, Chungbuk National University, Cheongju, Korea

Abstract

A novel and stereo-controlled method for the preparation of functionalized macrolactams was developed. The process involves stereoselective enol ether formation, followed by an azacyclic ring expansionvia an aza-Claisen rearrangement. Herewith, we describe a systematic investigation of an aza-Claisen rearrangement-induced ring expansion of azacycles prepared by appending E/Z-enol ethers to the medium-sized lactams as well as the stereochemical outcome. In addition, the strategy was successfully applied to the total synthesis of fluvirucinine A1 and 3-epi-fluvirucinine A1. This method offers an attractive alternative to the intramolecular amide–aldol reaction for the elaboration of β-alkoxy-α-substituted motifs.

Graphical abstract: A stereo-controlled access to functionalized macrolactams via an aza-Claisen rearrangement

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Article information

DOI
https://doi.org/10.1039/C1OB06733H
Article type
Paper
Submitted
14 Oct 2011
Accepted
24 Oct 2011
First published
25 Oct 2011

Org. Biomol. Chem., 2012,10, 561-568

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A stereo-controlled access to functionalized macrolactams via an aza-Claisen rearrangement

Y. Suh, Y. Lee, S. Kim, J. Jung, H. Yun, J. Jang, N. Kim and J. Jung, Org. Biomol. Chem., 2012, 10, 561 DOI: 10.1039/C1OB06733H

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