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Abstract:
Garsubellin A is a meroterpene capable of enhancing the enzyme choline acetyltransferase whose decreased level is believed to play a central role in the symptoms of Alzheimer's disease. Due to the potentially useful biological activity together with the novel bridged and fused cyclic molecular architecture, garsubellin A has garnered substantial synthetic interest, but its absolute stereostructure has been undetermined. We report here the first enantioselective total synthesis of (+)-garsubellin A. Our synthesis relies on stereoselective fashioning of a cyclohexanone framework and double conjugate addition of 1,2-ethanedithiol that promotes aldol cyclization to build the bicyclic [3.3.1] skeleton. The twelve-step, protecting group-free synthetic route has enabled the syntheses of both the natural (-)-garsubellin A and its unnatural (+)-antipode for biological evaluations.
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
ISSN: 1433-7851
Year: 2021
Issue: 42
Volume: 60
Page: 22735-22739
1 6 . 8 2 3
JCR@2021
1 6 . 1 0 0
JCR@2023
ESI Discipline: CHEMISTRY;
ESI HC Threshold:117
JCR Journal Grade:1
CAS Journal Grade:2
Cited Count:
WoS CC Cited Count: 9
SCOPUS Cited Count: 10
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 0
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