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Strathprints serves world leading Open Access research by the University of Strathclyde, including research by the Strathclyde Institute of Pharmacy and Biomedical Sciences (SIPBS), where research centres such as the Industrial Biotechnology Innovation Centre (IBioIC), the Cancer Research UK Formulation Unit, SeaBioTech and the Centre for Biophotonics are based.

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Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols

Alvarez-Dorta, D. and Leon, E.I. and Kennedy, A.R. and Riesco-Fagundo, C. and Suarez, E. (2008) Sequential norrish type ii photoelimination and intramolecular aldol cyclization of 1,2-diketones in carbohydrate systems: stereoselective synthesis of cyclopentitols. Agewandte Chemie-International Edition, 47 (46). pp. 8917-8919. ISSN 1433-7851

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Abstract

Opened and closed: Visible-light photostimulation of 2,3-diuloses I triggers an unprecedented sequential rearrangement: A Norrish type II photoelimination to give an isolable acyclic photoenol intermediate II is followed by an intramolecular enolexo aldolization. The contraction of the pyranose ring in this process leads to a new type of cyclopentitol derivative III. R=acyl, alkyl, silyl group.