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Synlett 2001; 2001(2): 0269-0271
DOI: 10.1055/s-2001-10761
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Montmorillonite K-10 Clay Assisted Transformation of Vinylketoses into Spirochromans and Arylketoses

Peter A. V. van Hooft* , Paul F. van Swieten, Gijsbert A. van der Marel, Constant A. A. van Boeckel, Jacques H. van Boom
  • *Leiden Institute of Chemistry, P.O. Box 9502, 2300 RA Leiden, The Netherlands; Fax +31 71 5274307; E-mail: j.boom§chem.leidenuniv.nl
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Publication Date:
31 December 2001 (online)

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Montmorillonite K-10 clay mediated synthesis of spirochromans and arylketoses starting from 1,2-dideoxy-4,5,6-tri-O-benzyl-8-O-tert-butyldimethylsilyl-d-gluco-oct-1-eno-3-ulopyranose (6) is presented. In addition, valuable chiral synthons were obtained by conversion of the spirochromans and arylketoses into the open chain derivatives via Vasella rearrangement.

aromatic Claisen rearrangement - Friedel-Crafts alkylation - Vasella rearrangement

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