Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 16, Pages 4030-4043Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200802069
Keywords
anticancer agents; cross-coupling; macrolides; natural products; structure-activity relationships
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Funding
- MPG
- Chemical Genomics Center
- Fonds der Chemischen Industrie
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Deliberate deviations front the previously described total syntheses of amphidinolide X (1) and Y (2) allowed a collection of seven designed analogues of these extremely scarce marine natural products to be obtained. These fully synthetic natural product-like Compounds enabled first insights into the previously unknown structure-activity relationships governing this series. Although the average cytotoxicity is moderate, it was found that Certain bladder, Colon and prostate cancer cell lines are fairly sensitive, and that the best synthetic analogues arc more active than the natural products themselves. The syntheses rely oil the 9-MeO-9-BBN variant of the Suzuki coupling for the formation of the carbon frameworks, as well as on Yamaouchi lactonization reactions for the cyclization of the macrocyclic rings.
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