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

Trembleau, Laurent;Patiny, Luc;Ghosez, Léon
(2000) Tetrahedron Letters — Vol. 41, n° 33, p. 6377-6381 (2000)

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Authors
  • Trembleau, LaurentUCLouvain
    Author
  • Patiny, LucUniversity of Lausanne
    Author
  • Ghosez, LéonUCLouvain
    Author
Abstract
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.
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Citations

Trembleau, L., Patiny, L., & Ghosez, L. (2000). Diels-Alder reactions of activated furans to cyclopentenone derivatives: a regiodivergent Diels-Alder approach towards polyfunctionalised cis-hydrindanones. Tetrahedron Letters, 41(33), 6377-6381. https://doi.org/10.1016/S0040-4039(00)01068-6 (Original work published 2000)