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Pure and Applied Chemistry

The Scientific Journal of IUPAC

Ed. by Burrows, Hugh / Stohner, Jürgen

12 Issues per year


IMPACT FACTOR 2017: 5.294

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1365-3075
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Volume 75, Issue 2-3

Issues

Biomimetic approach toward the stereoselective synthesis of acetogenins

R. V. A. Orru
  • Corresponding author
  • Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands
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/ Bas Groenendaal
  • Corresponding author
  • Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands
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/ J. van Heyst
  • Corresponding author
  • Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands
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/ Mark Hunting
  • Corresponding author
  • Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands
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/ C. Wesseling
  • Corresponding author
  • Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands
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/ R. F. Schmitz
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  • Department of Chemistry, Vrije University Amsterdam, De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands
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/ S. F. Mayer
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  • Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria
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/ K. Faber
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  • Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz, Austria
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Published Online: 2009-01-01 | DOI: https://doi.org/10.1351/pac200375020259

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.

Conference

IUPAC International Symposium on the Chemistry of Natural Products, International Symposium on the Chemistry of Natural Products, ISCNP, Natural Products, 23rd, Florence, Italy, 2002-07-28–2002-08-02

About the article

Published Online: 2009-01-01

Published in Print: 2003-01-01


Citation Information: Pure and Applied Chemistry, Volume 75, Issue 2-3, Pages 259–264, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/pac200375020259.

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