Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 42, Pages 11307-11318Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200901525
Keywords
anticancer agents; Australian tropical rainforests; natural products; total synthesis
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Funding
- EcoBiotics Ltd
- University of Queensland
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EBC-23, 24, 25, 72, 73, 75 and 76 were isolated from the fruit of Cinnamomum laubatii (family Lauraceae) in the Australian tropical rainforests. EBC-23 (1) was synthesized stereoselectively, in nine linear steps in 8% overall yield, to confirm the reported relative stereochemistry and determine the absolute stereochemistry. Key to the total synthesis was a series of Tietze-Smith linchpin reactions. The novel spiroacetal structural motif, exemplified by EBC-23 (1), was found to inhibit the growth of the androgen-independent prostate tumor cell fine DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults.
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