ORGN 726 |
| 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.
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
