Nine-Step Stereoselective Synthesis of Islatravir from Deoxyribose
| Autor: | Mark Weisel, Hongming Li, Teresa Andreani, Christopher C. Nawrat, Aaron M. Whittaker, David M. Tschaen, Mark A. Huffman, Ryan D. Cohen, Mark McLaughlin, Bangwei Ding |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Deoxyadenosines
010405 organic chemistry Stereochemistry Chemistry Deoxyribose Organic Chemistry Human immunodeficiency virus (HIV) Chromosomal translocation Stereoisomerism Silanes 010402 general chemistry medicine.disease_cause 01 natural sciences Biochemistry Reverse transcriptase 0104 chemical sciences chemistry.chemical_compound Alkynes medicine Reverse Transcriptase Inhibitors Stereoselectivity Physical and Theoretical Chemistry Nucleoside |
| Zdroj: | Organic letters. 22(6) |
| ISSN: | 1523-7052 |
| Popis: | A stereoselective nine-step synthesis of the potent HIV nucleoside reverse transcriptase translocation inhibitor (NRTTI) islatravir (EfdA, MK-8591) from 2-deoxyribose is described. Key findings include a diastereodivergent addition of an acetylide nucleophile to an enolizable ketone, a chemoselective ozonolysis of a terminal olefin and a biocatalytic glycosylation cascade that uses a unique strategy of byproduct precipitation to drive an otherwise-reversible transformation forward. |
| Databáze: | OpenAIRE |
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