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.
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
© 2013 Walter de Gruyter GmbH, Berlin/Boston
