1040726-60-0Relevant articles and documents
Studies on asymmetric synthesis of bicyclomycin precursors. A chemoenzymatic route to chiral 2,5-diketopiperazines and 2-oxa-bicyclo[4.2.2]decane-8,10-diones
Fryszkowska, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 1127 - 1134 (2017/09/15)
A novel asymmetric route to bicyclomycin analogues, 2-oxa-bicyclo[4.2.2]decane-8,10-diones, is described. The key chiral synthons 3-(ω-hydroxyalkyl)-2,5-diketopiperazines 3a-c were obtained via enzymatic kinetic resolution of their respective acetates 2a-c using hydrolases (up to >98% ee, E > 200). The chiral 2,5-diketopiperazines were then transformed into their bicyclic derivatives in a stereospecific manner. Circular dichroism and NMR studies were performed to determine the absolute and relative configuration of the obtained products. The biocatalytic approach gave high stereoselectivities in comparison to the chiral pool synthesis from glutamic acid (58% ee) and thus demonstrated the ability of hydrolases to discriminate a remote stereocenter.
Studies towards the synthesis of bicyclomycin precursors: Synthesis of N,N′-disubstituted 2,5-diketopiperazines in solution and on solid phase
Fryszkowska, Anna,Ostaszewski, Ryszard
, p. 765 - 772 (2008/09/21)
(Chemical Equation Presented) The synthesis of 3-(hydroxyalkyl)-N,N′- disubstituted 2,5-diketopiperazine derivatives - compounds required for the bicyclomycin analogues preparation - has been studied. The use of various oxo components in the Ugi multicomp
