Rh(I)-Catalyzed Allenic Pauson-Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity.
Journal
Organic letters
ISSN: 1523-7052
Titre abrégé: Org Lett
Pays: United States
ID NLM: 100890393
Informations de publication
Date de publication:
04 02 2022
04 02 2022
Historique:
pubmed:
27
1
2022
medline:
11
2
2022
entrez:
26
1
2022
Statut:
ppublish
Résumé
Thapsigargin (Tg) is a potent SERCA pump inhibitor with the potential to treat cancer and COVID-19. We have extended the scope of the asymmetric allenic Pauson-Khand reaction to furan-tethered allene-ynes, a stereoconvergent transformation affording the 5,7,5-ring system of Tg in good yields and high enantioselectivity. Computational studies of the oxidative cyclization step show that the furan and chloroacetate groups contribute to this high selectivity.
Identifiants
pubmed: 35081313
doi: 10.1021/acs.orglett.1c03951
doi:
Substances chimiques
Chloroacetates
0
Furans
0
Thapsigargin
67526-95-8
Rhodium
DMK383DSAC
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Langues
eng
Sous-ensembles de citation
IM
Pagination
995-999Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM128779
Pays : United States