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.

Castagnolo, D., Botta, L., Botta, M. (2009). Stereoselective protecting group free synthesis of D,L-gulose ethyl glycoside via multicomponent enyne cross methatesis-hetero Diels-Alder reaction. CARBOHYDRATE RESEARCH, 344, 1285-1288 [10.1016/j.carres.2009.05.007].

Stereoselective protecting group free synthesis of D,L-gulose ethyl glycoside via multicomponent enyne cross methatesis-hetero Diels-Alder reaction

CASTAGNOLO, DANIELE;BOTTA, LORENZO;BOTTA, MAURIZIO
2009-01-01

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.
Castagnolo, D., Botta, L., Botta, M. (2009). Stereoselective protecting group free synthesis of D,L-gulose ethyl glycoside via multicomponent enyne cross methatesis-hetero Diels-Alder reaction. CARBOHYDRATE RESEARCH, 344, 1285-1288 [10.1016/j.carres.2009.05.007].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11365/9221
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