A Biomimetic Enantioselective Approach to the Decahydroquinoline Class of Dendrobatid Alkaloids
2008; Wiley; Volume: 47; Issue: 18 Linguagem: Inglês
10.1002/anie.200705888
ISSN1521-3773
AutoresMercedes Amat, Rosa Griera, Robert Fabregat, Elı́es Molins, Joan Bosch,
Tópico(s)Advanced Synthetic Organic Chemistry
ResumoAngewandte Chemie International EditionVolume 47, Issue 18 p. 3348-3351 Communication A Biomimetic Enantioselective Approach to the Decahydroquinoline Class of Dendrobatid Alkaloids† Mercedes Amat Prof. Dr., Mercedes Amat Prof. Dr. [email protected] Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this authorRosa Griera Dr., Rosa Griera Dr. Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this authorRobert Fabregat, Robert Fabregat Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this authorElies Molins Dr., Elies Molins Dr. Institut de Ciència de Materials de Barcelona (CSIC), Campus UAB, 08193 Cerdanyola, SpainSearch for more papers by this authorJoan Bosch Prof. Dr., Joan Bosch Prof. Dr. [email protected] Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this author Mercedes Amat Prof. Dr., Mercedes Amat Prof. Dr. [email protected] Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this authorRosa Griera Dr., Rosa Griera Dr. Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this authorRobert Fabregat, Robert Fabregat Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this authorElies Molins Dr., Elies Molins Dr. Institut de Ciència de Materials de Barcelona (CSIC), Campus UAB, 08193 Cerdanyola, SpainSearch for more papers by this authorJoan Bosch Prof. Dr., Joan Bosch Prof. Dr. [email protected] Laboratory of Organic Chemistry, Faculty of Pharmacy and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain, Fax: (+34) 93-402-45-39 http://www.ub.edu/farmaco/grupos/amatbosch/indice.htmSearch for more papers by this author First published: 14 April 2008 https://doi.org/10.1002/anie.200705888Citations: 43 † Financial support from the Ministry of Science and Technology (Spain)-FEDER (Project CTQ2006-02390/BQU) and the DURSI, Generalitat de Catalunya (Grant 2005SGR-0603) is gratefully acknowledged. 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 princely synthesis: The hypothetical key step in the biosynthesis of the decahydroquinoline dendrobatid alkaloids, such as cis-195 A found in frogs, from 1,5-polycarbonyl derivatives is mimicked by using (R)-phenylglycinol as a chiral latent form of ammonia in a double cyclocondensation reaction. 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