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Anticancer Agents from the Australian Tropical Rainforest: Spiroacetals EBC‐23, 24, 25, 72, 73, 75 and 76
Author(s) -
Dong Lin,
Schill Heiko,
Grange Rebecca L.,
Porzelle Achim,
Johns Jenny P.,
Parsons Peter G.,
Gordon Victoria A.,
Reddell Paul W.,
Williams Craig M.
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901525
Subject(s) - rainforest , du145 , cinnamomum , chemistry , lauraceae , stereochemistry , biology , botany , medicine , prostate , pathology , alternative medicine , traditional chinese medicine , cancer , lncap , cassia
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.