Recent advances in the staudinger reaction

Synthesis of bicyclic tripeptides inspired by the ABC-ring system of vancomycin through ruthenium-based cyclization chemistries

“…22 Therefore, the second generation Hoveyda-Grubbs catalyst 23 was used in refluxing CH2Cl2 and macrocyclic peptide 8 was isolated in 55% yield as a mixture of the E/Z diastereoisomers, as shown in Scheme 3 (8a (Z):8b (E) = 1:2.3). After Boc removal both diastereoisomers 8ab could be separated by preparative HPLC and characterized as well as identified by NMR and LC-(HR)MS.…”

Efficient protocol to quinazolino[3,2-d][1,4]benzodiazepine-6,9-dione via Staudinger-aza-Wittig cyclization: application to synthesis of Asperlicin D

“…Therefore, azido and ester groups were selected to study the feasibility of intramolecular aza-Wittig cyclization [15][16][17][18] As shown in Scheme 2, our study commenced with the coupling of isatoic anhydride (10) with ethyl glycinate in dry acetonitrile followed by acylation with freshly prepared 2-azidobenzoyl chloride. This reaction furnished N-[N-(2-azidobenzoyl)-2-aminobenzoy]glycine ethyl ester 11, as a model substrate, in good yield (80%).…”

Design, Synthesis, and Evaluation of ω‐(Isothiocyanato)alkylphosphinates and Phosphine Oxides as Antiproliferative Agents

“…Synthesis of ethyl (w-isothiocyanatoalkyl)(diethoxymethyl)-phosphinates [43][44][45][46] As shown in Scheme 3, ethyl (diethoxymethyl)phosphinate (34) was subjectedt oar eactionw ith excesss odium metal. Sodium phosphinate thus formed was alkylatedi nsitu with 1,n-dibromoalkanes in THF.T he method established by Lecouvey and colleagues [55] was adapted here.…”