Naturally occurring scaffolds for compound library design: convenient access to bis-aryl 1-azaadamantanes carrying a vicinal amino alcohol motif
Author(s)
Taheri, Abuzar
Quinn, Ronald J
Krasavin, Mikhail
Griffith University Author(s)
Year published
2014
Metadata
Show full item recordAbstract
The vast majority of scaffolds found in natural products are absent from the currently available compound collections for biological screening. At the same time, scaffolds derived from natural products may have a distinct advantage over non-natural cores in terms of providing compounds endowed with biological activities and should be used extensively in screening library design. We have developed a synthetic approach to merging a naturally occurring 1-azaadamantane core with a vicinal amino alcohol moiety that is also common in natural product chemical space. The synthesis features diastereoselective epoxidation of racemic ...
View more >The vast majority of scaffolds found in natural products are absent from the currently available compound collections for biological screening. At the same time, scaffolds derived from natural products may have a distinct advantage over non-natural cores in terms of providing compounds endowed with biological activities and should be used extensively in screening library design. We have developed a synthetic approach to merging a naturally occurring 1-azaadamantane core with a vicinal amino alcohol moiety that is also common in natural product chemical space. The synthesis features diastereoselective epoxidation of racemic chiral 2,6-diaryl-4-methylene 1-azaadamantanes with subsequent SN2-type epoxide opening in aqueous isopropanol.
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View more >The vast majority of scaffolds found in natural products are absent from the currently available compound collections for biological screening. At the same time, scaffolds derived from natural products may have a distinct advantage over non-natural cores in terms of providing compounds endowed with biological activities and should be used extensively in screening library design. We have developed a synthetic approach to merging a naturally occurring 1-azaadamantane core with a vicinal amino alcohol moiety that is also common in natural product chemical space. The synthesis features diastereoselective epoxidation of racemic chiral 2,6-diaryl-4-methylene 1-azaadamantanes with subsequent SN2-type epoxide opening in aqueous isopropanol.
View less >
Journal Title
Tetrahedron Letters
Volume
55
Subject
Medicinal and biomolecular chemistry
Medicinal and biomolecular chemistry not elsewhere classified
Organic chemistry