A Diels-Alder Approach to Anthrapyran Antibiotics

Abstract A new entry to the synthesis of anthrapyran antibiotics has been accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model. The key step features a Diels-Alder reaction between a substituted 5-vinyl-3,4-dihydro-2H-pyran and naphthoquinone as the dienophile. The resul...

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Bibliographic Details
Published in:Synlett 2012-03, Vol.23 (5), p.768-772
Main Authors: Foulgoc, Laura, Sissouma, Drissa, Evain, Michel, Collet, Sylvain, Guingant, André
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Chemistry
Condensed benzenic and aromatic compounds
Condensed Matter
Exact sciences and technology
General aspects
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
letter
Materials Science
Medical sciences
Noncondensed benzenic compounds
Organic chemistry
Pharmacology. Drug treatments
Physics
Preparations and properties
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Summary:Abstract A new entry to the synthesis of anthrapyran antibiotics has been accomplished through the synthesis of a 4H-anthra[1,2-B]pyran-4,7,12-trione model. The key step features a Diels-Alder reaction between a substituted 5-vinyl-3,4-dihydro-2H-pyran and naphthoquinone as the dienophile. The resulting tetracyclic adduct is then processed towards the targeted trione in a few steps.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1290529