Design and synthesis of a conformationally restricted trans peptide isostere based on the bioactive conformations of saquinavir and nelfinavir
Date
2001
Authors
Edmonds, M.
Abell, A.
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Journal article
Citation
Journal of Organic Chemistry, 2001; 66(11):3747-3752
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Michael K. Edmonds and Andrew D. Abell
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Abstract
The design and synthesis of a new peptide isostere which contains a trans alkene core is described. The key step involves a Wadsworth-Emmons reaction between chiral aldehyde (2S)-9a and chiral phosphonate 7 under base-sensitive conditions to give a chiral enone (2R)-24a which was reduced to afford the desired trans alkene isosteres (2R,5R)-6a and (2R,5S)-6b (Scheme 6). A potential application of this isostere in the synthesis of HIV protease inhibitors is also discussed.
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Copyright © 2001 American Chemical Society