Issue 16, 2002
From the journal:

Chemical Communications

Biosynthesis inspired Diels–Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics

Christopher J. Moody,*a   Rachael A. Hughes,a   Stewart P. Thompsona  and  Lilian Alcarazb  

* Corresponding authors

a School of Chemistry, University of Exeter, Exeter, UK
E-mail: c.j.moody@ex.ac.uk

b Medicinal Chemistry Department, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, UK

Abstract

Reaction of serine derived 1-alkoxy-2-azadienes with dehydroalanine derived dienophiles results in Diels–Alder reaction and aromatisation to give 2,3,6-trisubstituted pyridines, thereby establishing the viability of the proposed biosynthetic route to the pyridine ring of the thiopeptide antibiotics originally proposed by Bycroft and Gowland.

Graphical abstract: Biosynthesis inspired Diels–Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics

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Article information

DOI
https://doi.org/10.1039/B204868J
Article type
Communication
Submitted
20 May 2002
Accepted
18 Jun 2002
First published
12 Jul 2002

Chem. Commun., 2002, 1760-1761

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Biosynthesis inspired Diels–Alder route to pyridines: synthesis of the 2,3-dithiazolylpyridine core of the thiopeptide antibiotics

C. J. Moody, R. A. Hughes, S. P. Thompson and L. Alcaraz, Chem. Commun., 2002, 1760 DOI: 10.1039/B204868J

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