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Intramolecular diels-alder reactions of the furan diene: substituent and solvent effects

✍ Scribed by Daniel D. Sternbach; Debby M. Rossana

Publisher: Elsevier Science
Year: 1982
Tongue: French
Weight: 262 KB
Volume: 23
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)86815-x

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✦ Synopsis

An internal Diels-Alder reaction, using furan as the diene component, formed a highly functionalized 5-membered carbocycllc ring in excellent yield.

Solvent and substituent effects of this reaction were examined.

In connection with a proJect devoted to the synthesis of some natural products containing 5membered carbocycllc rings we have been interested in developing a general method for the stereospecific synthesis of these ring systems.

To this end we have explored the intramolecular Diels-Alder reaction of substituted furans, where the furan II systems serve as the diene, and the dlenophile IS connected by a 3-carbon chain. While several examples of intramolecular Diels-Alder reactions with furans have been descnbedl, only one example of this particular type has been reported (eq. l)la.

In this case a 40% yield of product was achieved after -Q?? 0 ogt Eq. 1 refluxing the t-extant in benzene for 5 days.

In the same paper Parker et al. studied related Diels-Alder reactions in which the starting materials contained a heteroatom in the bridging chain. The conclusions reached in this paper and references therein are twofold 1. The yield

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