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Stereocontrolled Solid‐Phase Synthesis of a 90‐Membered Library of Indoline‐Alkaloid‐like Polycycles from an Enantioenriched Aminoindoline Scaffold

2005; Wiley; Volume: 44; Issue: 9 Linguagem: Inglês

10.1002/anie.200462298

ISSN

1521-3773

Autores

Zhonghong Gan, P. Thirupathi Reddy, Sophie Quevillon‐Chéruel, Samuel Couve‐Bonnaire, Prabhat Arya,

Tópico(s)

Quinazolinone synthesis and applications

Resumo

Angewandte Chemie International EditionVolume 44, Issue 9 p. 1366-1368 Communication Stereocontrolled Solid-Phase Synthesis of a 90-Membered Library of Indoline-Alkaloid-like Polycycles from an Enantioenriched Aminoindoline Scaffold† Zhonghong Gan Dr., Zhonghong Gan Dr. Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068Search for more papers by this authorP. Thirupathi Reddy Dr., P. Thirupathi Reddy Dr. Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068Search for more papers by this authorSophie Quevillon, Sophie Quevillon Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068 Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, K1N 6N5, CanadaSearch for more papers by this authorSamuel Couve-Bonnaire Dr., Samuel Couve-Bonnaire Dr. Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068Search for more papers by this authorPrabhat Arya Dr., Prabhat Arya Dr. [email protected] Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068 Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, K1N 6N5, CanadaSearch for more papers by this author Zhonghong Gan Dr., Zhonghong Gan Dr. Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068Search for more papers by this authorP. Thirupathi Reddy Dr., P. Thirupathi Reddy Dr. Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068Search for more papers by this authorSophie Quevillon, Sophie Quevillon Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068 Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, K1N 6N5, CanadaSearch for more papers by this authorSamuel Couve-Bonnaire Dr., Samuel Couve-Bonnaire Dr. Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068Search for more papers by this authorPrabhat Arya Dr., Prabhat Arya Dr. [email protected] Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, K1A 0R6, Canada, Fax: (+1) 613-952-0068 Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, K1N 6N5, CanadaSearch for more papers by this author First published: 15 February 2005 https://doi.org/10.1002/anie.200462298Citations: 70 † We sincerely thank Stuart Schreiber, Jared Shaw, and the DOS team members at the Broad Institute of Harvard and MIT for providing alkylsilyl-linker-based macrobeads and for their help in our solid-phase synthesis projects. This work was supported by a NRC genomics and health initiative program, special VP-NRC funds for chemical biology, the National Cancer Institute of Canada (NCIC), and the Canadian Institutes of Health Research (CIHR). Malgosia Daroszewska, Michael Barnes, and Don Leek are thanked for their technical support. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract A library of tricyclic derivatives, similar to indoline alkaloids, has been generated by using a stereocontrolled, conjugate hetero-Michael approach in both the solution and the solid phase (see scheme; P=protecting group, R=functional group). The mild reaction conditions that lead to the tricyclic derivatives, which contain β-amino acid functionalities, are highly attractive. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z462298_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. References 1 1aS. L. Schreiber, Chem. Eng. 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