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Sulfamidate-Based Stereoselective Total Synthesis of (+)-Preussin Using Gold(I)-Catalyzed Intramolecular Dehydrative Amination: Dead End and Detour

Title
Sulfamidate-Based Stereoselective Total Synthesis of (+)-Preussin Using Gold(I)-Catalyzed Intramolecular Dehydrative Amination: Dead End and Detour
Authors
Park Y.Ryu J.-S.
Ewha Authors
류재상박윤정
SCOPUS Author ID
류재상scopus; 박윤정scopus
Issue Date
2023
Journal Title
Journal of Organic Chemistry
ISSN
2232-3263JCR Link
Citation
Journal of Organic Chemistry vol. 88, no. 14, pp. 9902 - 9909
Publisher
American Chemical Society
Indexed
SCOPUS scopus
Document Type
Article
Abstract
A sulfamidate-based stereoselective total synthesis of (+)-preussin has been developed. The key step involves a gold(I)-catalyzed intramolecular dehydrative amination of sulfamate esters tethered to allylic alcohols, which allows for the construction of the cyclic sulfamidate with high stereoselectivity. Further manipulation to highly constrained bicyclic sulfamidate and the following ring-opening process afford 3-hydroxypyrrolidine motif stereoselectively. The energy of the constrained bicyclic ring system is relieved by the subsequent ring-opening process, which leads to a stereoselective formation of the 3-hydroxypyrrolidine motif under mild reaction conditions. The success of this approach not only provides a new method for the total synthesis of enantiomerically pure (+)-preussin but also highlights the synthetic utility of sulfamidates in constructing valuable natural product architectures. © 2023 American Chemical Society.
DOI
10.1021/acs.joc.3c00670
Appears in Collections:
약학대학 > 약학과 > Journal papers
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