1,3-Diazepanes of natural product-like complexity from cyanamide-induced rearrangement of epoxy-delta-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 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.
Dutta
Sanjay
S
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093, USA.
Higginson
Cody J
CJ
Ho
Bao T
BT
Rynearson
Kevin D
KD
Dibrov
Sergey M
SM
Hermann
Thomas
T
D001381:Azepines / Q000737:chemistry*; D003484:Cyanamide / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D007769:Lactams / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D001381:Azepines; D004852:Epoxy Compounds; D007769:Lactams; D003484:Cyanamide