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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 9
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Original Articles

The Intramolecular Diels-Alder Furan Approach in Synthesis : 11-oxatricyclo|6.2.1.01,6|undec-9-en-5-one

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Pages 771-780 | Received 30 May 1979, Published online: 05 Dec 2006
 

Abstract

Although the synthetic potential of the intramolecular variant of the Diels-Alder reaction has now been fully recognized3, little attention has so far been paid to this type of addition using the furan nucleus as the diene partner4–8. The presence of an oxygenated cyclohexene system in several complex natural products (e.g. gibberellic acid, morphine), the diverse possibilities of the substituted 7-oxabicyclo |2.2.1|-2-heptene system for further transformation9, the expected enhanced reactivity and stereoselectivity of the intramolecular cycloaddition and the availability of a wide variety of commercial furan derivatives make the sequence a → b → c particularly attractive in total synthesis.

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