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An Expedient Total Synthesis of Triciribine
- Source :
- Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry
- Publication Year :
- 2017
-
Abstract
- In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif.
- Subjects :
- Models, Molecular
triciribine
glycosylation
Stereochemistry
Pharmaceutical Science
Chemistry Techniques, Synthetic
ring closure
01 natural sciences
Analytical Chemistry
Nucleobase
Catalysis
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Drug Discovery
Trifluoroacetic acid
Physical and Theoretical Chemistry
total synthesis
Protein kinase B
Protein Kinase Inhibitors
chemistry.chemical_classification
Molecular Structure
010405 organic chemistry
Communication
Organic Chemistry
Regioselectivity
Total synthesis
Nucleosides
0104 chemical sciences
chemistry
Chemistry (miscellaneous)
030220 oncology & carcinogenesis
Molecular Medicine
Ribonucleosides
Nucleoside
Tricyclic
Subjects
Details
- ISSN :
- 14203049
- Volume :
- 22
- Issue :
- 4
- Database :
- OpenAIRE
- Journal :
- Molecules (Basel, Switzerland)
- Accession number :
- edsair.doi.dedup.....29e3abac26b12a4c39d6f370bae19123