Issue 16, 2002

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

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

Article information

Article type
Communication
Submitted
20 May 2002
Accepted
18 Jun 2002
First published
12 Jul 2002

Chem. Commun., 2002, 1760-1761

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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