A Concise Total Synthesis of (±)-Stepharine and (±)-Pronuciferine

Ruiming Chen; Shihu Jia; Yuning Man; Hong-Gang Cheng; Qianghui Zhou

doi:10.1055/a-1984-0755

Synthesis, Table of Contents

Synthesis 2024; 56(11): 1695-1701
DOI: 10.1055/a-1984-0755

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New Trends in Organic Synthesis from Chinese Chemists

A Concise Total Synthesis of (±)-Stepharine and (±)-Pronuciferine

Ruiming Chen‡

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China

,

Shihu Jia‡

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China

,

Yuning Man

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China

,

Hong-Gang Cheng ∗

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China

,

Qianghui Zhou∗

^aSauvage Center for Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials (Ministry of Education), Hubei Key Lab on Organic and Polymeric Opto-Electronic Materials, College of Chemistry and Molecular Sciences, The Institute for Advanced Studies, Wuhan University, 430072 Wuhan, P. R. of China

^bTaiKang Center for Life and Medical Sciences, Wuhan University, 430072 Wuhan, P. R. of China

^cState Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, 345 Ling Ling Rd, Shanghai 200032, P. R. of China

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Abstract

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Abstract

A concise total synthesis of (±)-stepharine and (±)-pronuciferine using readily available reagents as the starting materials is reported. This synthesis features a three-component Catellani reaction/Au-catalyzed 6-exo-dig cyclization for the assembly of 1-methylene-tetrahydroisoquinoline scaffold and an oxidative dearomatization for constructing spiro-cyclohexadienone scaffold.

Key words

stepharine - pronuciferine - 1-methylene-tetrahydroisoquinoline - Catellani reaction - total synthesis

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References

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