Article: Rh(I)-Catalyzed Allenic Pauson–Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups on Enantioselectivity
Organic letters. 2022 Jan. 26, v. 24, no. 4
2022
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 ... ...
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. |
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Keywords | COVID-19 infection ; Ca2-transporting ATPase ; cyclization reactions ; enantioselectivity ; furans |
Language | English |
Dates of publication | 2022-0126 |
Size | p. 995-999. |
Publishing place | American Chemical Society |
Document type | Article |
ISSN | 1523-7052 |
DOI | 10.1021/acs.orglett.1c03951 |
Database | NAL-Catalogue (AGRICOLA) |
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