Towards the total synthesis of colletofragarones: constructing the macrocyclic lactone by high pressure-mediated intramolecular Diels–Alder reaction
✍ Scribed by Joaquín G. Marrero; Laurence M. Harwood
- Publisher
- Elsevier Science
- Year
- 2009
- Tongue
- French
- Weight
- 418 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
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 conidia in these species.
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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
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