Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
Org Lett. 2010 Jan 15;12(2):360-3. doi: 10.1021/ol9026914.
A synthetic procedure toward 1,3-diazepane scaffolds of natural product-like complexity was developed for the construction of RNA-directed ligand libraries. A molecular building block was designed that combines the characteristics of RNA-binding natural products, including a high density of hydrogen bond donors and acceptors around a rigid, nonplanar scaffold with straightforward total-synthetic accessibility that permits extensive control over the chemical space. The synthesis of the 1,3-diazepane scaffold was achieved via an unprecedented cyanamide-induced rearrangement of epoxy-delta-lactams.
开发了一种合成具有类似天然产物复杂性的 1,3-二氮杂环戊烷骨架的方法，用于构建 RNA 导向配体文库。设计了一种分子构建块，它结合了 RNA 结合天然产物的特性，包括在刚性、非平面支架周围具有高密度的氢键供体和受体，以及具有简单总合成可及性，可对化学空间进行广泛控制。通过前所未有的氰酰胺诱导的环氧-δ-内酰胺重排，实现了 1,3-二氮杂环戊烷骨架的合成。
