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Synthesis 2006(10): 1673-1681
DOI: 10.1055/s-2006-926456
DOI: 10.1055/s-2006-926456
PAPER
© Georg Thieme Verlag Stuttgart · New York
Approach to the Eleutherobin Core: Synthesis of a Key Intermediate by Intramolecular Diels-Alder Cycloaddition
Further Information
Received
27 October 2005
Publication Date:
27 April 2006 (online)
Publication History
Publication Date:
27 April 2006 (online)
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Abstract
An attractive intermediate in the total synthesis of the eleutherobin core has been obtained. Both syn and anti aldol diastereoisomers were synthesized by two different diastereoselective reaction sequences from 5-methyl-4-(pyrrolydin-1′-yl)-5H-furan-2-one. Each diastereoisomer was esterified and subjected to an intramolecular Diels-Alder reaction, which led to an intermediate that possesses rings A and C of the eleutherobin skeleton.
Key words
aldol reactions - Diels-Alder reactions - antitumor agents - eleuthesides - diastereoselectivity
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References
Present address: Dipartimento di Chimica e Chimica Industriale Università di Pisa, Via Risorgimento 35, 56126 Pisa, Italy.