Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2024; 56(11): 1695-1701
DOI: 10.1055/a-1984-0755
DOI: 10.1055/a-1984-0755
feature
New Trends in Organic Synthesis from Chinese Chemists
A Concise Total Synthesis of (±)-Stepharine and (±)-Pronuciferine
Authors
We 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.
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 synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1984-0755.
- Supporting Information (PDF)
Publication History
Received: 29 October 2022
Accepted after revision: 22 November 2022
Accepted Manuscript online:
22 November 2022
Article published online:
06 February 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Bernauer K. Helv. Chim. Acta 1963; 46: 1783
- 1b Cava MP, Nomura K, Schlessinger RH, Buck KT, Douglas B, Raffauf RF, Weisbach JA. Chem. Ind. (London) 1964; 28: 282
- 2a Bhat SV, Bhattacharya BK, De Souza NJ, Dohadwalla AN, Kohl H. Ger. Offen. DE 2557282, 1977
- 2b Berezhinskaya VV, Trutneva EA. Tr. Vses. Nauchno-Issled. Inst. Lek. Rast. 1971; 14: 66
- 2c Hao T, Yang Y, Li N, Mi Y, Zhang G, Song J, Liang Y, Xiao J, Zhou D, He D, Hou Y. Phytomedicine 2020; 79: 153353
- 2d da Silva Mesquita R, Kyrylchuk A, Cherednichenko A, Costa Sa IS, Macedo Bastos L, Moura Araujo da Silva F, Saraiva Nunomura RC, Grafov A. Molecules 2022; 27: 3138
- 3a Bernauer KF. Helv. Chim. Acta 1963; 46: 1783
- 3b Bartley JP, Baker LT, Carvalho CF. Phytochemistry 1994; 36: 1327
- 3c Bayazeid O, Nemutlu E, Eylem CC, Yalçın FN. J. Biochem. Mol. Toxicol. 2020; 34: e22601
- 3d Yano M, Nakashima S, Oda Y, Nakamura S, Matsuda H. J. Nat. Med. 2020; 74: 212
- 3e Wang FX, Zhu N, Zhou F, Lin DX. Molecules 2021; 26: 6117
- 3f Ma C, Li G, He Y, Xu B, Mi X, Wang H, Wang Z. Life Sci. 2015; 136: 120
- 4 Bernauer K. Helv. Chim. Acta 1968; 51: 1119
- 5a Horii Z, Nakashita Y, Iwata C. Tetrahedron Lett. 1971; 1167
- 5b Horii Z, Iwata C, Nakashita Y. Chem. Pharm. Bull. 1978; 26: 481
- 6 Honda T, Shigehisa H. Org. Lett. 2006; 8: 657
- 7 Magnus P, Marks KD, Meis A. Tetrahedron 2015; 71: 3872
- 8a Kametani T, Sugahara T, Sugi H, Shibuya S, Fukumoto K. J. Chem. Soc. D 1971; 724
- 8b Kametani T, Sugahara T, Sugi H, Shibuya S, Fukumoto K. Tetrahedron 1971; 5993
- 9 Bai M, Jia S, Zhang J, Cheng H.-G, Cong H, Liu S, Huang Z, Huang Y, Chen X, Zhou Q. Angew. Chem. Int. Ed. 2022; 61: e20220524
- 10a Catellani M, Frignani F, Rangoni A. Angew. Chem. Int. Ed. 1997; 36: 119
- 10b Ye J, Lautens M. Nat. Chem. 2015; 7: 863
- 10c Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
- 10d Cheng H.-G, Chen S, Chen R, Zhou Q. Angew. Chem. Int. Ed. 2019; 58: 5832
- 10e Zhao K, Ding L, Gu Z. Synlett 2019; 30: 129
- 10f Wang J, Dong G. Chem. Rev. 2019; 119: 7478
- 10g Dong S, Luan X. Chin. J. Chem. 2021; 39: 1690
- 11a Hashmi AS. K. Chem. Rev. 2007; 107: 3180
- 11b Enomoto T, Obika S, Yasui Y, Takemoto Y. Synlett 2008; 1647
- 11c Huang L, Arndt M, Gooßen KT, Heydt H, Goossen LJ. Chem. Rev. 2015; 115: 2596
- 12 Qian G, Bai M, Gao S, Chen H, Zhou S, Cheng H.-G, Yan W, Zhou Q. Angew. Chem. Int. Ed. 2018; 57: 10980
- 13a Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
- 13b O’Brien CJ, Kantchev EA, Valente C, Hadei N, Chass GA, Lough A, Hopkinson AC, Organ MG. Chem. Eur. J. 2006; 12: 4743
- 13c Yajima A, Urao S, Yoshioka Y, Abe N, Katsuta R, Nukada T. Tetrahedron Lett. 2013; 54: 4986
- 13d Walker SD, Barder TE, Martinelli JR, Buchwald SL. Angew. Chem. Int. Ed. 2004; 43: 1907
- 13e Barder TE, Walker SD, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4685
- 14 Jia S, Bai M, Zhou S, Sheng R, Cheng H.-G, Zhou Q. ChemRxiv 2022; preprint
- 15 Al-Zoubi RM, Hall DG. Org. Lett. 2010; 12: 2480
- 16 Ogawa T, Ohta K, Iijima T, Suzuki T, Ohta S, Endo Y. Bioorg. Med. Chem. 2009; 17: 1109
- 17 Almeida M, Boman A, Lundstedt T. J. Labelled Compd. Radiopharm. 2002; 45: 371
- 18 Panteleev J, Huang RY, Lui EK, Lautens M. Org. Lett. 2011; 13: 5314