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author:

Jang, Dongseok (Jang, Dongseok.) [1] | Choi, Minchul (Choi, Minchul.) [2] | Chen, Jinglong (Chen, Jinglong.) [3] (Scholars:陈敬龙) | Lee, Chulbom (Lee, Chulbom.) [4]

Indexed by:

EI SCIE

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.

Keyword:

carbocycles carbonylation natural products PPAP total synthesis

Community:

  • [ 1 ] [Jang, Dongseok]Seoul Natl Univ, Dept Chem, Seoul 08826, South Korea
  • [ 2 ] [Choi, Minchul]Seoul Natl Univ, Dept Chem, Seoul 08826, South Korea
  • [ 3 ] [Lee, Chulbom]Seoul Natl Univ, Dept Chem, Seoul 08826, South Korea
  • [ 4 ] [Chen, Jinglong]Princeton Univ, Dept Chem, Princeton, NJ 08540 USA
  • [ 5 ] [Chen, Jinglong]Fuzhou Univ, Coll Mat Sci & Engn, Fuzhou 350108, Peoples R China

Reprint 's Address:

  • [Lee, Chulbom]Seoul Natl Univ, Dept Chem, Seoul 08826, South Korea

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Source :

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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