title: Solid-phase synthesis of diverse spiroisoxazolinodiketopiperazines.
abstract: A convenient, efficient protocol to prepare diverse spiroisoxazolino-diketopiperazines via a parallel solid-supported synthesis was developed. The key steps are (1) a coupling reaction of an amino acid; (2) tosylation with concomitant β-elimination to form an α, β-unsaturated ester; (3) a 1,3-dipolar cycloaddition with an oxime to form isoxazoline rings; and (4) cyclic cleavage to release the product from the resin. All reaction steps and workup procedures were modified to allow the use of automated or semiautomated equipment. A 100-member demonstration library with two diversity sites was prepared in good purity and acceptable overall yields.
authors.affiliation: The Genomics Research Center, Academia Sinica , No. 128, Academia Road Sec. 2, Nankang District, Taipei, 11529, Taiwan.
authors.forename: Yi-Wen
authors.initials: YW
authors.lastname: Pan
authors.forename: Chih-Wei
authors.initials: CW
authors.lastname: Guo
authors.forename: Huang-Yao
authors.initials: HY
authors.lastname: Tu
authors.forename: Chih-Wei
authors.initials: CW
authors.lastname: Tsai
authors.forename: Wei-Chieh
authors.initials: WC
authors.lastname: Cheng
mesh_terms: D008956:Models, Chemical; D010879:Piperazines / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D010879:Piperazines