Total Synthesis of (+)‐trans‐Trikentrin A |
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Authors: | Iris R. M. Tébéka Giovanna B. Longato Dr. Marcus V. Craveiro Prof. João E. de Carvalho Dr. Ana L. T. G. Ruiz Prof. Luiz F. Silva Jr. |
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Affiliation: | 1. Instituto de Química, Universidade de S?o Paulo, CP 26077 CEP 05513‐970 S?o Paulo‐SP (Brazil), Fax: (+55 11) 3815‐5579;2. Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas, Universidade Estadual de Campinas, Campinas‐SP (Brazil);3. Present address: Universidade Federal de S?o Paulo, R. Prof. Artur Riedel, 275 CEP 09972‐270 Diadema‐SP (Brazil) |
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Abstract: | 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. |
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Keywords: | antitumor activity kinetic resolution ring contraction total synthesis trikentrin |
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