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

Authors
Trembleau, L Patiny, L Ghosez, L
Citation
L. Trembleau et al., Diels-Alder reactions of activated furans to cyclopentenone derivatives: aregiodivergent Diels-Alder approach towards polyfunctionalised cis-hydrindanones, TETRAHEDR L, 41(33), 2000, pp. 6377-6381
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
33
Year of publication
2000
Pages
6377 - 6381
Database
ISI
SICI code
0040-4039(20000812)41:33<6377:DROAFT>2.0.ZU;2-5
Abstract
Cycloaddition of activated furans 10 to 4-methoxycyclopent-2-enone was unex pectedly found to take place with a regioselectivity opposed to that predic ted by FMO theory. The reaction represents a direct route towards polyfunct ionalised cis-hydrindanones which are key intermediates for the synthesis o f ottelione A, a potent inhibitor of tubulin polymerisation. (C) 2000 Elsev ier Science Ltd. All rights reserved.