Optically Active γ-Hydroxy Sulfone Julia Reagents for the Synthesis of Peptidyl Olefin Peptidomimetics

✍ Scribed by Sima Mirilashvili; Naama Chasid-Rubinstein; Amnon Albeck

• Book ID: 102173079
• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: English
• Weight: 121 KB
• Volume: 2008
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200800334

✦ Synopsis

Abstract

Peptidyl olefin peptidomimetics serve as biologically active compounds or as intermediates for other peptidyl isosteres. We developed a chemoenzymatic stereoselective approach to optically active γ‐hydroxy sulfones to be assembled into peptidyl olefins by the Julia reaction. Key enzymatic hydrolysis of prochiral diesters to the corresponding hydroxy esters introduces optical activity. The sequence of the subsequent chemical reactions, either protection–hydrolysis–functionalization or functionalization–hydrolysis–protection, determines the absolute stereochemistry of the final sulfone building block.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)