Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 4, Issue 10, Pages 1977-2002Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b603015g
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The design and synthesis of spiroketal structures and their chemical modi. cation, leading to a collection of new small molecules for biological evaluation as orally-bioavailable lead compounds is described. Both [6,5]- and [6,6]-membered ring spiroketal units have been prepared in a stereochemically-varying fashion starting from commercially available ( R)- or ( S)- glycidol, in ten, eleven and twelve linear steps, in overall yields of 45, 40 and 20%, respectively. Further elaboration according to Lipinski's guidelines has given a collection of structurally-diverse, new spiroketal derivatives in high yields and with high purity.
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