One-pot hydrosilylation-protodesilylation of functionalized diarylalkynes: a highly selective access to Z-stilbenes. Application to the synthesis of combretastatin A-4 |
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| Authors: | Anne Giraud,Abdallah Hamzé ,Jean-Daniel Brion,Mouâ d Alami |
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| Affiliation: | a Univ Paris-Sud, BioCIS, UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.B. Clément, Châtenay-Malabry F-92296, France
b CNRS, BioCIS, UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, rue J.B. Clément, Châtenay-Malabry F-92296, France |
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| Abstract: | An efficient stereoselective synthesis of Z-stilbenes has been developed from diarylalkynes via a new hydrosilylation-protodesilylation process. The scope and limitation of this method is presented to stereoselectively prepare a wide range of (Z)-stilbenes in a one-pot way is presented. A concise application to the preparation of combretastatin A-4 (CA-4), a vascular targeting agent inhibitor of tubulin polymerisation is described. |
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| Keywords: | Combretastatin A-4 (Z)-Stilbenes Hydrosilylation Desilylation Platinum |
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