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Synlett 2021; 32(20): 1981-1986
DOI: 10.1055/a-1650-4266
synpacts

Enantioselective Palladium-Catalyzed Decarboxylative Dearomative Asymmetric Allylic Alkylation of Benzofurans: Diversity-Oriented Synthesis of Flavaglines

Hai-Hua Lu  ∗
a   Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, P. R. of China
b   Institute of Natural Sciences, Westlake Institute for Advanced Study, Hangzhou 310024, P. R. of China
c   Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, P. R. of China
d   Institute of Advanced Synthesis (IAS), Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. of China
,
Meng-Yue Cao
a   Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, P. R. of China
b   Institute of Natural Sciences, Westlake Institute for Advanced Study, Hangzhou 310024, P. R. of China
c   Department of Chemistry, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058, P. R. of China
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (NNSFC 21772090) and Young Scholar 1000 Talents Plan of China.
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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 condensation


Publication 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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