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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• 作者：S. Werner ; D.M. Turner ; P.G. Chambers ; K.M. Brummond
• 关键词：Library design ; Skeletal diversity ; Appendage diversity ; Polycycles ; Diels– ; Alder reaction
• 刊名：Tetrahedron
• 出版年：2008
• 出版时间：14 July 2008
• 年：2008
• 卷：64
• 期：29
• 页码：6997-7007
• 全文大小：887 K

文摘

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.