Stereoselective protecting group free synthesis of d,l-gulose ethyl glycoside via multicomponent enyne cross metathesis—hetero Diels–Alder reaction

Castagnolo, Daniele, Botta, Lorenzo and Botta, Maurizio (2009) Stereoselective protecting group free synthesis of d,l-gulose ethyl glycoside via multicomponent enyne cross metathesis—hetero Diels–Alder reaction. Carbohydrate Research, 344 (11). pp. 1285-1288. ISSN 0008-6215

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Official URL: http://dx.doi.org/10.1016/j.carres.2009.05.007

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.

Item Type: Article
Uncontrolled Keywords: gulose, stereoselective synthesis, microwave, hexose
Subjects: F100 Chemistry
Department: Faculties > Health and Life Sciences > Applied Sciences
Depositing User: Linda Barlow
Date Deposited: 09 Jan 2013 11:26
Last Modified: 24 Oct 2017 11:37
URI: http://nrl.northumbria.ac.uk/id/eprint/10982

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