Contribution to the total synthesis of caribenolide I |
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Authors: | Gaë l Jalce,Blandine Seon-Meniel |
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Affiliation: | Laboratoire de Pharmacognosie associé au CNRS (BioCIS), Faculté de Pharmacie, Université Paris-Sud, rue Jean-Baptiste Clément, 92296 Châtenay Malabry, France |
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Abstract: | Stereoselective synthesis of C13-C29 fragment of caribenolide I, a potent antitumour macrolide isolated from a marine dinoflagellate Amphidinium sp. is described. The key step relies on a highly diastereoselective C-glycosylation, using a bulky chiral oxazolidin-2-thione, to control the absolute configuration of C21. The C24 and C25 stereogenic centres were controlled by the enantioselective vinylogous Mukayiama aldol reaction, whereas C14 and C16 stereogenic centres were built from a chiral bis-epoxide. |
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