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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
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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