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Diels-Alder reactions of activated furans to cyclopentenone derivatives: a regiodivergent Diels-Alder approach towards polyfunctionalised cis-hydrindanones

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Trembleau, Laurent [UCL] Patiny, Luc [University of Lausanne] Ghosez, Léon [UCL]

Cycloaddition of activated furans 10 to 4-methoxycyclopent-2-enone was unexpectedly found to take place with a regioselectivity opposed to that predicted by FMO theory. The reaction represents a direct route towards polyfunctionalised cis-hydrindanones which are key intermediates for the synthesis of ottelione A, a potent inhibitor of tubulin polymerisation. (C) 2000 Elsevier Science Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2000
Language Anglais
Journal information "Tetrahedron Letters" - Vol. 41, no. 33, p. 6377-6381 (2000)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4039
e-issn 1873-3581
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords cis-hydrindanones ; cycloadditions ; furans ; high-pressure chemistry ; otteliones
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Bibliographic reference Trembleau, Laurent ; Patiny, Luc ; Ghosez, Léon. Diels-Alder reactions of activated furans to cyclopentenone derivatives: a regiodivergent Diels-Alder approach towards polyfunctionalised cis-hydrindanones. In: Tetrahedron Letters, Vol. 41, no. 33, p. 6377-6381 (2000)
Permanent URL http://hdl.handle.net/2078.1/43338