1,3-Diazepanes of Natural Product-Like Complexity from Cyanamide-Induced Rearrangement of Epoxy-δ-lactams

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...

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Bibliographic Details
Published in:Organic letters 2010-01, Vol.12 (2), p.360-363
Main Authors: Dutta, Sanjay, Higginson, Cody J, Ho, Bao T, Rynearson, Kevin D, Dibrov, Sergey M, Hermann, Thomas
Format: Article
Language:English
Subjects:
Azepines - chemistry
Cyanamide - chemistry
Epoxy Compounds - chemistry
Hydrogen Bonding
Lactams - chemistry
Molecular Conformation
Stereoisomerism
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Summary: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-δ-lactams.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9026914