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

Laurent Alain Claude Trembleau, Luc Patiny, Leon Ghosez

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22 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)6377-6381
JournalTetrahedron Letters
Volume41
Issue number33
Publication statusPublished - 2000

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Tubulin Modulators
Furans
Regioselectivity
Cycloaddition
Cycloaddition Reaction
Derivatives
ottelione A
cyclopentenone

Cite this

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title = "Diels-Alder reactions of activated furans to cyclopentenone derivatives: A regiodivergent Diels-Alder approach towards polyfunctionalised cis-hydrindanones",
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.",
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AU - Trembleau, Laurent Alain Claude

AU - Patiny, Luc

AU - Ghosez, Leon

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Y1 - 2000

N2 - 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.

AB - 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.

M3 - Article

VL - 41

SP - 6377

EP - 6381

JO - Tetrahedron Letters

JF - Tetrahedron Letters

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