Anticancer Agents from the Australian Tropical Rainforest: Spiroacetals EBC‐23, 24, 25, 72, 73, 75 and 76 |
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| Authors: | Lin Dong Dr Heiko Schill Dr Rebecca?L Grange Dr Achim Porzelle Dr Jenny?P Johns Peter?G Parsons Dr Victoria?A Gordon Dr Paul?W Reddell Dr Craig?M Williams Dr |
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| Institution: | 1. School of Chemistry and Molecular Biosciences, University of Queensland, Brisbane, 4072, Queensland (Australia);2. EcoBiotics Limited, PO Box 1, Yungaburra, 4884, Queensland (Australia) www.ecobiotics.com.au;3. Queensland Institute of Medical Research, PO Royal Brisbane Hospital, Brisbane, 4029, Queensland (Australia) |
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| Abstract: | 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 line DU145 in the mouse model, indicating potential for the treatment of refractory solid tumors in adults. |
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| Keywords: | anticancer agents Australian tropical rainforests natural products total synthesis |
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