Partner und Internationale Organisationen
(Englisch)
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B, CH, CRO, CZ, D, DK, E, F, FIN, H, I, IRL, N, NL, P, PL, S, SI, UK
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Abstract
(Englisch)
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Furan and 2,3-dimethylfuran add to optically pure 1-cyanovinyl esters to give homochiral Diels-Alder adducts ('naked sugars') that are powerful starting materials (chirons) for the synthesis of natural products, analogues and compounds of biological interest. The group in Lausanne has made use of the 7-oxa ring opening methodology invented in Madrid to realize polypropionate fragments as found in several antibiotics. It has applied the new method of Cossy for the reductive ring opening of 7-oxanorbornan-2-ones to the synthesis of the first examples of C-galactosides of carbapentoses, new disaccharide mimics that have a potential as glycosidase inhibitors or as biological tools in the decoding of cellular language. The group at ESPCI has continued to use the 'naked sugars of the first generation' to develop extremely efficient total asymmetric syntheses of natural products including ethisolide, isoavenaciolide and the skeleton of eriolanin. The group at ENSCP together with the Lausanne group has studied the aryl- and vinylpalladation of the 'naked sugars'. It was discovered that these reactions that introduce two different carbon chains at C(5) and C(6) of 7-oxanorborn-5-en-2-yl derivative are not only highly face selective but also regioselective. The regioselectivity is controlled by the substituent at C(2). This discovery opens an alternative route to the synthesis of taxol and analogues and sets new basis to understand the Heck reaction. The group in Madrid has continued to apply the 'naked sugar' technology to the synthesis of all kinds of products of biological interest. The oxa ring opening method they have studied is a powerful technique that can be applied in a predictive way to all kinds of 7-oxanorbornane systems and that leads to complicated products with high yields and stereoselectivities. The work done in Madrid and Paris is a powerful valorization of the 'naked sugars' which opens new avenues to the asymmetric synthesis starting with inexpensive furans. This collaboration program has produced 31 publications in internationally renown journals.
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