A Straightforward Diastereoselective
Synthesis and Evaluation of Climacostol, A Natural Product with
Anticancer Activities

Dennis Fiorini; Sandra Giuli; Enrico Marcantoni; Luana Quassinti; Massimo Bramucci; Consuelo Amantini; Giorgio Santoni; Federico Buonanno; Claudio Ortenzi

doi:10.1055/s-0029-1218695

PAPER

A Straightforward Diastereoselective Synthesis and Evaluation of Climacostol, A Natural Product with Anticancer Activities

Dennis Fiorini^a, Sandra Giuli^a, Enrico Marcantoni*^a, Luana Quassinti^b, Massimo Bramucci^b, Consuelo Amantini^c, Giorgio Santoni^c, Federico Buonanno^d, Claudio Ortenzi*^d
^a School of Sciences and Technologies, Section of Chemistry, University of Camerino, via S. Agostino 1, 62032 Camerino (MC), Italy
Fax: +39(0737)402297; e-Mail: enrico.marcantoni@unicam.it;
^b School of Pharmacy, Physiology, University of Camerino, via Gentile III da Varano, 62032 Camerino (MC), Italy
^c School of Pharmacy, Anatomy Unit, University of Camerino, via Scalzino 3, 62032 Camerino (MC), Italy
^d Department of Educational Sciences and Training, University of Macerata, P. le Bertelli 1, 62100 Macerata, Italy
e-Mail: claudio.ortenzi@unimc.it;

Abstract

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Abstract

On the basis of continued interest in plant-derived natural products as anticancer agents, a shorter and more efficient synthesis of climacostol is reported. This compound showed an anticancer activity better than that of the natural product. The improved potency and selectivity can be due to the absence of traces of the undesired E-isomer present in the natural climacostol. Furthermore, the versatile strategy developed for this simple molecule such as climacostol could aid in the synthesis of other more complex natural products.

Key words

bioorganic chemistry - C-C bond formation - diastereoselectivity - natural products - protecting groups - Wittig reaction

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Referenzen

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