Skeletal and appendage diversity as design elements in the synthesis of a discovery library of nonaromatic polycyclic 5-iminooxazolidin-2-ones, hydantoins, and acylureas |
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Authors: | S Werner DM Turner PG Chambers KM Brummond |
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Institution: | Center for Chemical Methodologies and Library Development (UPCMLD), University of Pittsburgh, Pittsburgh, PA 15260, USA |
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Abstract: | Amino-acid derived cross-conjugated trienes were used as a starting point for the synthesis of a discovery library of over 200 polycyclic 5-iminooxazolidin-2-ones, hydantoins, and acylureas. The main feature of this library synthesis is a triple branching strategy, which provides efficient access to five skeletally diverse scaffolds. In addition, four sets of building blocks were applied in both a front end and a back end diversification strategy. Multiple fused rings were obtained by cyclization of diamides with phosgene and stereoselective Diels-Alder reactions with maleimides. The 5-iminooxazolidin-2-one scaffold was rearranged into the isomeric hydantoin scaffold through a sequence of ring-opening and ring-closing reactions. |
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Keywords: | Library design Skeletal diversity Appendage diversity Polycycles Diels-Alder reaction |
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