Rh(I)-Catalyzed Allenic Pauson-Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity.
Org Lett
; 24(4): 995-999, 2022 02 04.
Article
in English
| MEDLINE | ID: covidwho-1655437
ABSTRACT
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.
Full text:
Available
Collection:
International databases
Database:
MEDLINE
Main subject:
Rhodium
/
Thapsigargin
Type of study:
Experimental Studies
/
Randomized controlled trials
Language:
English
Journal:
Org Lett
Journal subject:
Biochemistry
Year:
2022
Document Type:
Article
Affiliation country:
Acs.orglett.1c03951
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