The Diels-Alder adduct of furfuryl alcohol and maleic anhydride was converted into dimethyl 5-exo,6-exo-dihydroxy-1{[tris (isopropyl)silyloxy] methyl} -7-oxabicyclo[2.2.1]heptane-2-exo,3-exo-dicarboxylate (12). Regioselective monosilylation of diol 12 gave the 5-O-(tert-butyl)dimethylsilyl ether 18. Under basic conditions the 7-oxanorbornane system of 18 was isomerized selectively into a 4,5,6-trihydroxy-6-(hydroxymethyl)cyclohex-2-ene-1,2-dicarboxylic derivative that was converted into a doubly-branched hepturonic acid derivative (24), potential precursor for the preparation of squalestatin core analogues.
Type
research article
Authors
Publication date
1999
Published in
Issue
12
Start page
1883
End page
1886
Note
Univ Lausanne, Chim Sect, BCH, CH-1015 Lausanne, Switzerland.
Peer reviewed
REVIEWED
EPFL units
Available on Infoscience
November 9, 2005
Use this identifier to reference this record