Efficient synthesis of the bis(tetrahydrofuran) ring core of trilobin and trilobacin and progress toward the synthesis of the natural products

AEI 69

Laura M. Wysocki, lmwysocki@wisc.edu and Steven D. Burke, burke@chem.wisc.edu. Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI 53706
Annonaceous Acetogenins are a class of compounds with a wide variety of biological activity. Trilobin and trilobacin, which exhibit potent antitumor activity, were the first of this class isolated with a cis/erythro/trans relative configuration about the bis(tetrahydrofuran) ring core. Starting from meso symmetric diol 1, the desymmetrized central ring system (2) was achieved in good yield and excellent selectivity via ring opening/cross metathesis using Grubbs' 2nd generation ruthenium benzylidene catalyst, followed by Pd(0) mediated double cycloetherification using Trost's (R, R)-DPPBA ligand and N(Hex)4Cl additive. Efforts toward the elaboration of 2 in the synthesis of trilobin and trilobacin will be discussed.

 

Academic Employment Initiative
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Academic Employment Initiative

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006