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‡
a   Sauvage 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‡
a   Sauvage 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
a   Sauvage 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  ∗
a   Sauvage 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∗
a   Sauvage 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
b   TaiKang Center for Life and Medical Sciences, Wuhan University, 430072 Wuhan, P. R. of China
c   State 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
› Author AffiliationsWe thank the National Natural Science Foundation of China (Grants 21801193, 21871213, and 22071189), Natural Science Foundation of Jiangsu Province (Grant No. BK20210119, H.-G. C.), the Fundamental Research Funds for the Central Universities (2042021kf0214) and the start-up funding from Wuhan University for financial support.
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1984-0755.
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Publication History

Received: 29 October 2022

Accepted after revision: 22 November 2022

Accepted Manuscript online:
22 November 2022

Article published online:
06 February 2023

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