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Synlett 2021; 32(20): 1981-1986
DOI: 10.1055/a-1650-4266
DOI: 10.1055/a-1650-4266
synpacts
Enantioselective Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation of Benzofurans: Diversity-Oriented Synthesis of Flavaglines
Authors
This work was supported by the National Natural Science Foundation of China (NNSFC 21772090) and Young Scholar 1000 Talents Plan of China.
Dedicated to Professor Wen-Jing Xiao on the occasion of Teachers’ Day
Abstract
With the introduction of new Trost-type bisphosphine ligands bearing a chiral cycloalkane framework, the highly efficient and enantioselective palladium-catalyzed decarboxylative dearomative asymmetric allylic alkylation (AAA) of benzofurans was achieved. This enabled a diversity-oriented synthesis (DOS) of previously unreachable flavaglines, which features two diversification stages. A new avenue for developing flavagline-based drugs was thus established.
1 Introduction
2 The Dearomative Asymmetric Allylic Alkylation of Benzofurans
3 Synthesis of Flavaglines
4 Conclusion and Outlook
Key words
palladium catalysis - dearomative asymmetric allylic alkylation (AAA) - total synthesis - flavaglines - diversity-oriented synthesis (DOS) - N-heterocyclic carbene (NHC) catalysis - benzoin condensationPublication History
Received: 09 September 2021
Accepted after revision: 21 September 2021
Accepted Manuscript online:
21 September 2021
Article published online:
08 October 2021
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