Stereoselective protecting group free synthesis of D,L-gulose ethyl glycoside via multicomponent enyne cross metathesis--hetero Diels-Alder reaction.
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
Daniele
D
Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, via A. de Gasperi 2, 53100 Siena, Italy.
Botta
Lorenzo
L
Botta
Maurizio
M
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008872:Microwaves; D013237:Stereoisomerism; D013379:Substrate Specificity
D006027:Glycosides; C544209:ethyl guloside