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Synthesis 2009(12): 2009-2014  
DOI: 10.1055/s-0029-1216824
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Cyclobutanols and Cyclopentane Dimers via Samarium(II) Iodide Induced Keto-Olefin Cyclisations of Carbohydrate-Derived Unsaturated Ketones

D. Bradley G. Williams*, Judy Caddy, Kevin Blann, J. J. Cronjé Grové, Cedric W. Holzapfel
Department of Chemistry, University of Johannesburg, P.O. Box 524, Auckland Park, Johannesburg 2006, South Africa
Fax: +27(11)4892819; e-Mail: bwilliams@uj.ac.za;
Further Information

Publication History

Received 18 February 2009
Publication Date:
19 May 2009 (online)

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Abstract

Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer.

Key words

carbocycles - carbohydrates - radical reactions - samarium - ring closure

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