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Published Online August 12, 2004
Science DOI: 10.1126/science.1101710

Reports

Submitted on June 21, 2004
Accepted on July 22, 2004

Two-Step Synthesis of Carbohydrates by Selective Aldol Reactions

Alan B. Northrup 1 and David W. C. MacMillan 1*

1 Department of Chemistry, California Institute of Technology, 1200 E California Boulevard, Pasadena, CA 91125, USA.

* To whom correspondence should be addressed.
David W. C. MacMillan , E-mail: dmacmill{at}caltech.edu

Studies of carbohydrates have been hampered by the lack of chemical strategies for the expeditious construction and coupling of differentially protected monosaccharides. Here, a synthetic route based on aldol coupling of three aldehydes is presented for the de novo production of polyol differentiated hexoses in only two chemical steps. The dimerization of {alpha}-oxyaldehydes, catalyzed by L-proline, is then followed by a tandem Mukaiyama aldol addition-cyclization step catalyzed by a Lewis acid. Differentially protected glucose, allose, and mannose stereoisomers can each be selected, in high yield and stereochemical purity, simply by changing the solvent and Lewis acid used. The reaction sequence also efficiently produces 13C-labelled analogs, as well as structural variants such as 2-amino- and 2-thio-substituted derivatives.


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Science. ISSN 0036-8075 (print), 1095-9203 (online)