Nine-Step Stereoselective Synthesis of Islatravir from Deoxyribose.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
20 03 2020
20 03 2020
Historique:
pubmed:
29
2
2020
medline:
11
6
2021
entrez:
29
2
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32108487
doi: 10.1021/acs.orglett.0c00239
doi:
Substances chimiques
Alkynes
0
Deoxyadenosines
0
Reverse Transcriptase Inhibitors
0
Silanes
0
Deoxyribose
533-67-5
islatravir
QPQ082R25D
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM