Synthesis of 1-Hydroxypyrrolidin-2,5-dione Derivatives of the Phosphonic–Hydroxamic Acid Antibiotic SF-2312
Wamuyu Owotoki A , Detlef Geffken A and Thomas Kurz A BA Institute of Pharmacy, University of Hamburg, 20146 Hamburg, Germany.
B Corresponding author. Email: kurz@chemie.uni-hamburg.de
Australian Journal of Chemistry 59(4) 283-288 https://doi.org/10.1071/CH06058
Submitted: 21 February 2006 Accepted: 12 April 2006 Published: 1 May 2006
Abstract
Analogues of the antibiotic SF-2312 with a 3-substituted 1-hydroxypyrrolidine moiety have been prepared from 1-benzyloxy-3-bromopyrrolidin-2,5-dione (1) through Michaelis–Arbusov reaction with various trialkyl phosphites and subsequent alkylation of ring position 3. Cleavage of phosphonic esters 3 by TMSBr afforded the corresponding phosphonic acids 7, which were treated with ethanolamine to give the monosalts 8. Finally, hydrogenolysis furnished 1-hydroxypyrrolidin-2,5-diones 9.
Acknowledgements
Financial support from the Grant of HmbNFG, Hamburg, Germany, is gratefully acknowledged.
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