Biomimetic approach toward the stereoselective synthesis of acetogenins
R. V. A. Orru, B. Groenendaal, J. van Heyst, M. Hunting, C. Wesseling, R. F. Schmitz, S. F. Mayer, and K. Faber
1Department of Chemistry, Vrije University Amsterdam,
De Boelelaan 1083, NL-1081 HV, Amsterdam, The Netherlands; 2Department
of Chemistry, University of Graz, Heinrichstrasse 28, A-8010, Graz,
Abstract: 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.
*Pure Appl.Chem. 75,
141419 (2003). An issue of reviews and research papers based on
lectures presented at the 23rd IUPAC International Symposium on the
Chemistry of Natural Products, Florence, Italy, 28 July 2 August 2002.
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