Optically Active γ??Hydroxy Sulfone Julia Reagents for the Synthesis of Peptidyl Olefin Peptidomimetics
S Mirilashvili, N Chasid??Rubinstein…
Index: Mirilashvili, Sima; Chasid-Rubinstein, Naama; Albeck, Amnon European Journal of Organic Chemistry, 2008 , # 20 p. 3461 - 3464
Full Text: HTML
Citation Number: 4
Abstract
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, ...
Related Articles:
[Mirilashvili, Sima; Chasid-Rubinstein, Naama; Albeck, Amnon European Journal of Organic Chemistry, 2010 , # 24 p. 4671 - 4686]
Unique template effects of distannoxane catalysts in transesterification of diol esters
[Otera, Junzo; Dan-oh, Nobuhisa; Nozaki, Hitosi Tetrahedron, 1993 , vol. 49, # 15 p. 3065 - 3074]
Acyclic stereoselection. 25. Stereoselective synthesis of the C-1 to C-7 moiety of erythronolide A
[Heathcock, Clayton H.; Young, Steven D.; Hagen, James P.; Pilli, Ronaldo; Badertscher, Ulrich Journal of Organic Chemistry, 1985 , vol. 50, # 12 p. 2095 - 2105]
[Brown, Herbert C.; Chen, Jackson C. Journal of Organic Chemistry, 1981 , vol. 46, # 20 p. 3978 - 3988]