Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antfinflammatory agent mangicol A
A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladiu...
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Published in | Tetrahedron Vol. 62; no. 22; pp. 5178 - 5194 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
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Abstract | A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved. |
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AbstractList | A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is the enantiopure cyclopentenecarboxylic acid 16. Of the several approaches targeting the 1,3-diene component 56, only that involving palladium-catalyzed enyne cyclization proved successful. Following the coupling of 16 to 56, we were unable to bring about any detectable level of (4 pi+2 pi) cycloaddition. Activation of the diene by incorporation of an OSiEt3 substituent on a terminal sp(2)-hybridized center likewise proved unsuccessful. Further facilitation was sought in the form of cyclopentenonecarboxylate 66. However, thermal activation, Lewis acid catalysis, and high-pressure conditions proved ineffective and did not lead to C-C bond formation. These studies serve to underscore the extent to which steric complications can complicate matters and the extent to which they must be skirted to arrive at the title compound. (c) 2006 Elsevier Ltd. All rights reserved. |
Author | Basu, Kallol Pichlmair, Stefan de Lera Ruiz, Manuel Paquette, Leo A. |
Author_xml | – sequence: 1 givenname: Stefan surname: Pichlmair fullname: Pichlmair, Stefan – sequence: 2 givenname: Manuel surname: de Lera Ruiz fullname: de Lera Ruiz, Manuel – sequence: 3 givenname: Kallol surname: Basu fullname: Basu, Kallol – sequence: 4 givenname: Leo A. surname: Paquette fullname: Paquette, Leo A. email: paquette.1@osu.edu |
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Cites_doi | 10.1021/ja012495d 10.1021/jo0344790 10.1021/ja020091v 10.1021/ja016378u 10.1002/anie.200200534 10.1002/anie.200351750 10.1002/cbic.200300651 10.1016/B978-0-08-052349-1.00131-1 10.1021/ol049308b 10.1021/ol047987k 10.1021/jo0264372 10.1021/ol0361047 10.1021/jo010751z 10.1039/b305068h 10.1021/ja0167405 10.1021/ol036308n 10.1021/ja0494149 10.1021/cr980054f 10.1055/s-2004-834866 |
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Keywords | CONVENIENT SYNTHESIS ORGANIC-SYNTHESIS ASYMMETRIC-SYNTHESIS ACID DIELS-ALDER REACTIONS ENANTIOSELECTIVE SYNTHESIS intramolecular aldol cyclizations EFFICIENT SYNTHESIS PD-CATALYZED CYCLOISOMERIZATION mangicols enantioselective diene synthesis chiral nonracemic substituted cyclopentadienones ALLYLIC ALCOHOLS Pd-catalyzed enyne cyclization KINETIC RESOLUTION |
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Snippet | A plan for enantioselective construction of the mangicol A framework by means of intramolecular Diels-Alder cycloaddition is outlined. First to be assembled is... |
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SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
Title | Evaluation of possible intramolecular [4+2] cycloaddition routes for assembling the central tetracyclic core of the potent marine antfinflammatory agent mangicol A |
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