Issue 42, 2015
From the journal:

Organic & Biomolecular Chemistry

Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels–Alder reaction†

A. R. Healya  and  N. J. Westwood*a  

* Corresponding authors

a School of Chemistry & Biomedical Sciences Research Complex, University of St Andrews & EaStCHEM, North Haugh, St Andrews, UK
E-mail: njw3@st-andrews.ac.uk

Abstract

A late stage Diels–Alder reaction is used to prepare a mixture of JBIR-22, a natural product from the Equisetin family of tetramic acids, and one of its diastereomers. This is achieved in just 8 steps from pyruvate. The success of the late stage DA approach is discussed in the context of the biosynthesis of JBIR-22 (and perhaps related natural products).

Graphical abstract: Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels–Alder reaction

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Article information

DOI
https://doi.org/10.1039/C5OB01771H
Article type
Paper
Submitted
01 Apr 2015
Accepted
25 Aug 2015
First published
02 Sep 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 10527-10531

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Synthetic studies on the bioactive tetramic acid JBIR-22 using a late stage Diels–Alder reaction

A. R. Healy and N. J. Westwood, Org. Biomol. Chem., 2015, 13, 10527 DOI: 10.1039/C5OB01771H

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