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Total Synthesis of (+)‐ trans ‐Trikentrin A
Author(s) -
Tébéka Iris R. M.,
Longato Giovanna B.,
Craveiro Marcus V.,
de Carvalho João E.,
Ruiz Ana L. T. G.,
Silva Luiz F.
Publication year - 2012
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.201202413
Subject(s) - stereochemistry , natural product , kinetic resolution , stereoselectivity , indole test , chemistry , total synthesis , combinatorial chemistry , biochemistry , enantioselective synthesis , catalysis
Several syntheses have already been reported for cis ‐trikentrins and herbindoles, which are indole alkaloids unsubstituted at the C2 and C3 positions that bear a trans ‐1,3‐dimethylcyclopentyl unit. Herein, we describe the first asymmetric and stereoselective synthesis of the more challenging trans ‐trikentrin A as its naturally occurring isomer. Different approaches were investigated and the strategy of choice was a combination of an enzymatic kinetic resolution and a thallium(III)‐mediated ring contraction. The antiproliferative activities of the natural product and related intermediates have been tested against human tumor cell lines, leading to the discovery of new compounds with potent antitumor activity.