Edmonds, M.Abell, A.2007-07-052007-07-052001Journal of Organic Chemistry, 2001; 66(11):3747-37520022-32631520-6904http://hdl.handle.net/2440/34863Copyright © 2001 American Chemical SocietyThe 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.enNelfinavirSaquinavirHIV Protease InhibitorsAnti-HIV AgentsIndicators and ReagentsMagnetic Resonance SpectroscopySpectrometry, Mass, Electrospray IonizationMolecular ConformationJournal article002006449010.1021/jo00168340001689113000132-s2.0-003535607450265Abell, A. [0000-0002-0604-2629]