The General Asymmetric Synthesis of syn‐ and anti‐β‐Substituted Cysteine and Serine Derivatives

Abstract

For Abstract see ChemInform Abstract in Full Text.

Peptidomimetics, a synthetic tool of drug discovery

“…A method for the asymmetric synthesis of compound 3 ( Figure 1) with either an anti or syn β-substituent was also developed [29]. The key intermediate of this method is a chiral aziridine that was synthesized from an α,β-unsaturated ester employing the Sharpless asymmetric dihydroxylation.…”

“…Indolizidine-2-one and -9-one amino acids, representing 6,5 and 5,6 scaffolds, were used as β-turn scans to explore the conformational requirements for activity of analogues of Calcitonin-gene related peptide (CGRP) antagonist, together with aza-aminoacid scans [32]. The importance of a type II' β-turn centered at Gly 33 [27][28][29][30][31][32][33][34][35][36][37] has been illustrated by increased antagonistic potency of the azaGly 33 and indolizidine-2-one amino acid [33][34] analogues. In addition, the improved metabolic stability and longer duration of action qualifies those scans to be another peptidomimetic research tool.…”

Synthesis and in vitro activities of new non‐peptidic APA Inhibitors

“…On the basis of this preliminary study we decided to study the compound 10 in more detail through the synthesis of the different stereoisomers to measure the inhibitory potency of each and thus to determine the stereopreference of APA for these new inhibitors. This was achieved by using an asymmetric synthesis of β‐substituted cysteines (12) (Fig. 3).…”

Synthesis of Salinosporamide A and Its Analogs as 20S Proteasome Inhibitors and SAR Summarization

“…The synthesis is outline in Scheme 4 [48]. The known alcohol 25 [49] was converted to oxazolidinone 26 [50] (93% yield) by successive acylation, reduction of the azide group and cyclization. Addition of 27 with 1-chloro-N,N-2-trimethylpropenylamine and 28 steroselectively led to formation of the -lactam 29.…”