Stereoselective protecting group free synthesis of d,l-gulose ethyl glycoside via multicomponent enyne cross metathesis—hetero Diels-Alder reaction |
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| Authors: | Daniele Castagnolo Maurizio Botta |
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| Affiliation: | a Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, via A. de Gasperi 2, 53100 Siena, Italy
b Sbarro Institute for Cancer Research and Molecular Medicine, Center for Biotechnology, College of Science and Technology, Temple University, BioLife Science Bldg., Suite 333, 1900 N 12th Street, Philadelphia, PA 19122, USA |
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| Abstract: | An efficient and stereoselective synthesis of d,l-gulose was described. The key step of the synthetic route is represented by a multicomponent enyne cross metathesis—hetero Diels-Alder reaction which allows the formation of the pyran ring from cheap and commercially available substrates in a single synthetic step. The synthesis of d,l-gulose was accomplished without the use of protecting groups making this approach highly desirable also in terms of atom economy. |
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| Keywords: | Gulose Stereoselective synthesis Microwave Hexose |
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