caa a22 4500 378866206 CHVBK 20180305123358.0 cr unu---uuuuu 161128e20030101xx s 000 0 eng 10.1351/pac200375020259 doi (NATIONALLICENCE)gruyter-10.1351/pac200375020259 Biomimetic approach toward the stereoselective synthesis of acetogenins [Elektronische Daten] [R. V. A. Orru, Bas Groenendaal, J. van Heyst, Mark Hunting, C. Wesseling, R. F. Schmitz, S. F. Mayer, K. Faber] Acetogenins isolated from the Annonaceae family of tropical trees have drawn considerable attention owing to their broad spectrum of biological activities. They are structurally characterized by the presence of one to three tetrahydrofuran rings in the center of a long (partly hydroxylated) hydrocarbon chain that ends in a (functionalized) butenolide moiety. Here we describe some of our results toward the first asymmetric total synthesis of cis-gigantrionenin, a principal acetogenin. In this approach, an enzyme-catalyzed epoxide hydrolysis and an enzyme-triggered double cyclization are crucial and give stereoselective access to essential chiral building blocks. © 2013 Walter de Gruyter GmbH, Berlin/Boston Orru R. V. A. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut Groenendaal Bas Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut van Heyst J. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut Hunting Mark Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut Wesseling C. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut Schmitz R. F. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut Mayer S. F. Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria aut Faber K. Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria aut Pure and Applied Chemistry De Gruyter 75/2-3(2003-01-01), 259-264 0033-4545 75:2-3<259 2003 75 pac https://doi.org/10.1351/pac200375020259 text/html Onlinezugriff via DOI 1 research article jats NATIONALLICENCE 856 40 https://doi.org/10.1351/pac200375020259 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Orru R. V. A. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut NATIONALLICENCE 700 1- Groenendaal Bas Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut NATIONALLICENCE 700 1- van Heyst J. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut NATIONALLICENCE 700 1- Hunting Mark Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut NATIONALLICENCE 700 1- Wesseling C. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut NATIONALLICENCE 700 1- Schmitz R. F. Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands aut NATIONALLICENCE 700 1- Mayer S. F. Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria aut NATIONALLICENCE 700 1- Faber K. Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria aut NATIONALLICENCE 773 0- Pure and Applied Chemistry De Gruyter 75/2-3(2003-01-01), 259-264 0033-4545 75:2-3<259 2003 75 pac CC0 http://creativecommons.org/publicdomain/zero/1.0 nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-gruyter