Abstract: Angewandte ChemieVolume 119, Issue 30 p. 5754-5756 Highlight Schutzgruppenfreie Totalsynthese komplexer cyanobakterieller Alkaloide Karl Gademann Prof. Dr., Karl Gademann Prof. Dr. [email protected] Chemical Synthesis Laboratory, Swiss Federal Institute of Technology, 1015 Lausanne, Schweiz, Fax: (+41) 21-693-9700 http://isic.epfl.ch/lsyncSearch for more papers by this authorSimone Bonazzi M.Sc., Simone Bonazzi M.Sc. Chemical Synthesis Laboratory, Swiss Federal Institute of Technology, 1015 Lausanne, Schweiz, Fax: (+41) 21-693-9700 http://isic.epfl.ch/lsyncSearch for more papers by this author Karl Gademann Prof. Dr., Karl Gademann Prof. Dr. [email protected] Chemical Synthesis Laboratory, Swiss Federal Institute of Technology, 1015 Lausanne, Schweiz, Fax: (+41) 21-693-9700 http://isic.epfl.ch/lsyncSearch for more papers by this authorSimone Bonazzi M.Sc., Simone Bonazzi M.Sc. Chemical Synthesis Laboratory, Swiss Federal Institute of Technology, 1015 Lausanne, Schweiz, Fax: (+41) 21-693-9700 http://isic.epfl.ch/lsyncSearch for more papers by this author First published: 13 July 2007 https://doi.org/10.1002/ange.200701881Citations: 10Read the full textAboutPDF ToolsRequest permissionAdd to favorites 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 Es geht auch ohne: Die Synthese der marinen Alkaloide Hapalindol U, Ambiguin, Fischerindol und Welwitindolinon (siehe Strukturen) gelang ohne die Verwendung von Schutzgruppen. Stattdessen wurde die intrinsische Reaktivität der empfindlichen Isonitrilgruppe in einer eleganten Reaktionssequenz zum Aufbau der Strukturgerüste genutzt. References 1Eine Übersicht hierzu: T. W. Greene, P. G. Wuts, Protective Groups in Organic Synthesis, 3. Aufl., Wiley, Hoboken, 1999. 10.1002/0471220574 Google Scholar 2S. Pitsch, Chimia 2001, 55, 320. CASWeb of Science®Google Scholar 3Eine Übersicht hierzu: M. A. Sierra, M. C. de la Torre, Dead Ends and Detours. Direct Ways to Successful Total Synthesis, Wiley, Weinheim, 2004. Google Scholar 4R. W. Hoffmann, Synthesis 2006, 3531. 10.1055/s-2006-950311 CASWeb of Science®Google Scholar 5 5aP. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404; 10.1038/nature05569 CASPubMedWeb of Science®Google Scholar 5bJ. A. Porco, Jr. Nature 2007, 446, 383. 10.1038/446383a CASPubMedWeb of Science®Google Scholar 6 6aA. M. Burja, B. Banaigs, E. Abou-Mansour, J. G. Burgess, P. C. Wright, Tetrahedron 2001, 57, 9347; 10.1016/S0040-4020(01)00931-0 CASWeb of Science®Google Scholar 6bK. Gademann, Chimia 2006, 60, 841. 10.2533/chimia.2006.841 CASWeb of Science®Google Scholar 7 7aK. Stratmann, R. E. Moore, R. Bonjouklian, J. B. Deeter, G. M. L. Patterson, S. Shaffer, C. D. Smith, T. A. Smitka, J. Am. Chem. Soc. 1994, 116, 9935; 10.1021/ja00101a015 CASWeb of Science®Google Scholar 7bR. E. Moore, C. Cheuk, G. M. L. Patterson, J. Am. Chem. Soc. 1984, 106, 6456; 10.1021/ja00333a079 CASWeb of Science®Google Scholar 7cR. E. Moore, C. Cheuk, X. G. Yang, G. M. L. Patterson, R. Bonjouklian, T. A. Smitka, J. S. Mynderse, R. S. Foster, N. D. Jones, J. K. Swartzendruber, J. B. Deeter, J. Org. Chem. 1987, 52, 1036; 10.1021/jo00382a012 CASWeb of Science®Google Scholar 7dT. A. Smitka, R. Bonjouklian, L. Doolin, N. D. Jones, J. B. Deeter, W. Y. Yoshida, M. R. Prinsep, R. E. Moore, G. M. L. Patterson, J. Org. Chem. 1992, 57, 857; 10.1021/jo00029a014 CASWeb of Science®Google Scholar 7eA. Raveh, S. Carmeli, J. Nat. Prod. 2007, 70, 196. 10.1021/np060495r CASPubMedWeb of Science®Google Scholar 8 8aH. Muratake, H. Kumagami, M. Natsume, Tetrahedron 1990, 46, 6351; 10.1016/S0040-4020(01)96007-7 CASWeb of Science®Google Scholar 8bP. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2004, 126, 7450; 10.1021/ja047874w CASPubMedWeb of Science®Google Scholar 8cP. S. Baran, J. M. Richter, J. Am. Chem. Soc. 2005, 127, 15394; 10.1021/ja056171r CASPubMedWeb of Science®Google Scholar 8dS. E. Reisman, J. M. Ready, A. Hasuoka, C. J. Smith, J. L. Wood, J. Am. Chem. Soc. 2006, 128, 1448; 10.1021/ja057640s CASPubMedWeb of Science®Google Scholar 8eJ. M. Ready, S. E. Reisman, M. Hirata, M. M. Weiss, K. Tamaki, T. V. Osaka, J. L. Wood, Angew. Chem. 2004, 116, 1290–1292; 10.1002/ange.200353282 Google ScholarAngew. Chem. Int. Ed. 2004, 43, 1270. 10.1002/anie.200353282 CASPubMedWeb of Science®Google Scholar 9Hoffmann wies darauf hin, dass bei der Synthese von 8 die Ketogruppe in situ geschützt wird; siehe Lit. [4]. Google Scholar 10R. Robinson, J. Chem. Soc. 1917, 111, 762. 10.1039/CT9171100762 CASWeb of Science®Google Scholar 11D. H. R. Barton, A. M. Deflorin, O. E. Edwards, J. Chem. Soc. 1956, 530. 10.1039/jr9560000530 CASWeb of Science®Google Scholar 12E. Hardegger, F. Lohse, Helv. Chim. Acta 1957, 40, 2383. 10.1002/hlca.19570400735 CASWeb of Science®Google Scholar Citing Literature Volume119, Issue30July 23, 2007Pages 5754-5756 This is the German version of Angewandte Chemie. Note for articles published since 1962: Do not cite this version alone. Take me to the International Edition version with citable page numbers, DOI, and citation export. We apologize for the inconvenience. ReferencesRelatedInformation
Publication Year: 2007
Publication Date: 2007-07-13
Language: de
Type: article
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