A variety of substituted furans a-6J undergo the intramolecular Die&Alder reaction at high pressure (12.5 kbar) to provide oxatricyclo adducts Q-12) within 24 hours at room temperature.
The high pressure mediated intramolecular diels-alder reaction of furans: Factors controlling cycloaddition with monoactivated dienophiles.
β Scribed by Laurence M. Harwood; Sarah A. Leeming; Neil S. Isaacs; Geraint Jones; John Pickard; Royston M. Thomas; David Watkin
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 313 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The Intramolecular Diels-Alder reactions of furans possessing a 2-alkyl substituent with a terminal @unsaturated ketone have been surveyed. The consequences of varying the degree of substitution of the furan, the bridging chain length, and position of the activating group on the dienophile upon the ease and stereochemistry of cycloaddition are reported.
π SIMILAR VOLUMES
The stereochemical outcome of intramolecular Diels-Alder reactions of furans with Z-and E-2-ene-1,4-dione units attached by a bridging chain to C-2 of the furan results from modification of the steric demands of the bridging chain by the preference of the external activating group to adopt an endost
We report herein an intramolecular Diels-Alder approach towards the construction of the macrocyclic lactone ring and the perhydrobenzofuran system of the colletofragarones, novel metabolites produced by fungi of the genus Colletotrichum that are responsible for inhibition of germination of the conid