First Total Syntheses of 1-Benzoyl-3,4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation

doi:10.6023/cjoc201912002

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (5): 1281-1289.DOI: 10.6023/cjoc201912002 Previous Articles Next Articles

Special Issue: 有机光催化虚拟合辑

基于光氧化反应的1-苯甲酰基-3,4-二氢异喹啉类生物碱Nelumstemine和Longifolonine的首次全合成

黄永康^a, 解文静^a, 罗永强^a, 范琪琦^a, 朱星亮^a, 刘世领^b, 施小新^a

a 华东理工大学药学院制药工程与过程化学教育部工程研究中心上海 200237;
b 青平药业有限公司上海 201710

收稿日期:2019-12-02 修回日期:2020-01-10 发布日期:2020-02-15
通讯作者: 刘世领, 施小新 E-mail:xxshi@ecust.edu.cn;liushiling@tenrypharm.com
基金资助:
国家自然科学基金（Nos.20972048，20172015）资助项目.

First Total Syntheses of 1-Benzoyl-3,4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation

Huang Yongkang^a, Xie Wenjing^a, Luo Yongqiang^a, Fan Qiqi^a, Zhu Xingliang^a, Liu Shiling^b, Shi Xiaoxin^a

a Engineering Research Center of Pharmaceutical Process Chemistry of the Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai 200237;
b Qingping Pharmaceutical Company Limited, Shanghai 201710

Received:2019-12-02 Revised:2020-01-10 Published:2020-02-15
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20972048, 20172015).

1. 201281S.pdf(1282KB)

Abstract

A novel synthetic route for the total syntheses of 1-benzoyl-3,4-dihydroisoquinoline alkaloids was developed. Nelumstemine was synthesized for the first time via 6 steps in 50% overall yield starting from 3,4-dimethoxybenzaldehyde, and longifolonine was also synthesized for the first time via 9 steps in 35% overall yield starting from vanillin. The key step of these total syntheses is photo-oxidation of 1-benzyl-3,4-dihydroisoquinolines to 1-benzoyl-3,4-dihydroisoquinolines by air under visible-light irradiation at room temperature. The unique mild photo-oxidation of 1-benzyl-3,4-dihydro-isoquinolines has been studied in detail.

Key words: benzoyl dihydroisoquinoline alkaloids, photo-oxygenation, nelumstemine, longifolonine

Cite this article

Huang Yongkang, Xie Wenjing, Luo Yongqiang, Fan Qiqi, Zhu Xingliang, Liu Shiling, Shi Xiaoxin. First Total Syntheses of 1-Benzoyl-3,4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation[J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1281-1289.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Marinho, A. F.; Oliveira, E. D. J.; Tavares, J. F.; Filho, R. B.; Barbosa-Filho, J. M. Magn. Reson. Chem. 2013, 51, 312.
(b) Sulaiman, S. N.; Mukhtar, M. R.; Hadi, A. H. A.; Awang, K.; Hazni, H.; Zahari, A.; Litaudon, M.; Zaima, K.; Morita, H. Molecules 2011, 16, 3119.
(c) Dang, Y.; Gong, H. F.; Liu, J. X.; Yu, S. J. Chin. Chem. Lett. 2009, 20, 1218.
(d) Zhang, H.; Yue, J.-M. Nat. Prod. Res. 2006, 20, 553.
(e) Chen, B.; Feng, C.; Li, B.-G.; Zhang, G.-L. Nat. Prod. Res. 2003, 17, 397.
(f) Lira, G. A. d.; Andrade, L. M. d.; Florencio, K. C.; Silva, M. S. d.; Barbosa-Filho, J. M.; da-Cunha, E. V. L. Fitoterapia 2002, 73, 356.
(g) Lebceuf, M.; Ranaivo, A.; Cave, A.; Moskowitz, H. J. Nat. Prod. 1989, 52, 516.
(h) Valencia, E.; Weiss, I.; Shamma, M.; Urzua, A.; Fajardo, V. J. Nat. Prod. 1984, 47, 1050.
[2] Duan, X. H.; Jiang, J. Q. Chin. Chem. Lett. 2008, 19, 308.
[3] Bick, I. R. C.; Sevenet, T.; Sinchai, W.; Skelton, B. W.; White, A. H. Aust. J. Chem. 1981, 34, 195.
[4] Nishiyama, Y.; Moriyasu, M.; Ichimaru, M.; Iwasa, K.; Kato, A.; Mathenge, S. G.; Mutiso, P. B. C.; Juma, F. D. Phytochemistry 2006, 67, 2671.
[5] (a) Salim, A. A.; Bidin, N.; Lafi, A. S.; Huyop, F. Z. Mater. Design 2017, 132, 486.
(b) Yogendra, K. N.; Dhokane, D.; Kushalappa, A. C.; Sarmiento, F.; Rodriguez, E.; Mosquera, T. Plant Sci. 2017, 256, 208.
(c) Bermejo, A.; Andreu, I.; Suvire, F.; Leonce, S.; Caignard, D. H.; Renard, P.; Pierre, A.; Enriz, R. D.; Cortes, D.; Cabedo, N. J. Med. Chem. 2002, 45, 5058.
[6] Yang, J.; Dong, J.; Lu, X.; Zhang, Q.; Ding, W.; Shi, X. Chin. J. Chem. 2012, 30, 2827.
[7] Crestey, F.; Jensen, A. A.; Borch, M.; Andreasen, J. T.; Andersen, J.; Balle, T.; Kristensen, J. L. J. Med. Chem. 2013, 56, 9673.
[8] Jetter, M. C.; Youngman, M. A.; McNally, J. J; McDonnell, M. E.; Zhang, S.-P.; Dubin, A. E.; Nasser, N.; Codd, E. E.; Flores, C. M.; Dax, S. L. Bioorg. Med. Chem. Lett. 2007, 17, 6160.
[9] (a) Sotomayor, N.; Dominguez, E.; Late, E. J. Org. Chem. 1996, 61, 4062.
(b) Morrison, G. C.; Cetenko, W.; Shavel Jr., J. J. Org. Chem. 1964, 29, 2771.
(c) Lu, X.; Meng, T.; Zheng, B.; Zhang, Y.; Wu, J.; Shi, X. Chin. J. Org. Chem. 2017, 37, 2663(in Chinese). (吕霞, 孟天卓, 郑波, 张义, 吴家家, 施小新, 有机化学, 2017, 37, 2663.)
[10] Ullah, S.; Park, C.; Ikram, M.; Kang, D.; Lee, S.; Yang, J.; Park, Y.; Yoon, S.; Chun, P.; Moon, H. R. Bioorg. Chem. 2019, 87, 43.
[11] Mastihubova, M.; Polakova, M. Beilstein J. Org. Chem. 2016, 12, 524.
[12] (a) Taylor, W. I. Tetrahedron 1961, 14, 42.
(b) Martin, N. H.; Champion, S. L.; Belt, P. B. Tetrahedron Lett. 1980, 21, 2613.
(c) Kessar, S. V.; Mohammad, T.; Gupta, Y. P. Indian J. Chem., Sect. B 1983, 22, 321.
(d) Kuo, R.-Y.; Chang, F.-R.; Wu, C.-C.; Patnam, R.; Wang, W.-Y.; Du, Y.-C.; Wu, Y.-C. Bioorg. Med. Chem. Lett. 2003, 13, 2789.
(e) Lenz, G. R.; Costanza, C. J. Org. Chem. 1988, 53, 1176.
(f) Martin, N. H.; Jefford, C. W. Helv. Chim. Acta 1982, 65, 762.
(g) Wakchaure, P. B.; Argade, N. P. Synthesis 2008, 2321.
(h) Andreu, I.; Cabedo, N.; Atassi, G.; Pierre, A.; Caignard, D. H.; Renard, P.; Cortes, D.; Bermejo, A. Tetrahedron Lett. 2002, 43, 757.
[13] Awuah, E.; Capretta, A. J. Org. Chem. 2010, 75, 5627.
[14] Garcia, M. D.; Wilson, A. J.; Emmerson, D. P. G.; Jenkins, P. R. Chem. Commun. 2006, 2586.
[15] (a) Clark, R. A.; Parker, D. C. J. Am. Chem. Soc. 1971, 93, 7257.
(b) Lu, S.-P.; Lewin, A. H. Tetrahedron 1998, 54, 15097.
[16] Choi, M. F.; Hawkins, P. Spectrochim. Acta 1995, 51A, 579.
[17] (a) Bayer, P.; Perez-Ruiz, R.; Wangelin, A. J. V. ChemPhotoChem 2008, 2, 559.
(b) Tambosco, B.; Segura, K.; Seyrig, C.; Cabrera, D.; Port, M.; Ferroud, C.; Amara, Z. ACS Catal. 2018, 8, 4383.
[18] (a) Maeda, K.; Nakamura, M.; Sakai, M. J. Chem. Soc., Perkin Trans. 1 1983, 837.
(b) Mori, Y.; Maeda, K. Bull. Chem. Soc. Jpn. 1994, 67, 1204.
[19] Rice, K. C.; Brossi, A. J. Org. Chem. 1980, 45, 592.
[20] Rozwadowska, M. D.; Chrzanowska, M.; Brossi, A.; Creveling, C. R.; Bembenek, M. E.; Abell, C. W. Helv. Chim. Acta 1988, 71, 1598.
[21] Zhu, R.; Xu, Z.; Ding, W.; Liu, S.; Shi, X.; Lu, X. Chin. J. Chem. 2014, 32, 1039.
[22] Weisbach, J. A.; Kirkpatrick, J. L.; Macko, E.; Douglas, B. J. Med. Chem. 1968, 11, 752.
[23] Zhao, B.-X.; Yu, Y.; Eguchi, S. Org. Prep. Proc. Int. 1997, 29,185.

基于光氧化反应的1-苯甲酰基-3,4-二氢异喹啉类生物碱Nelumstemine和Longifolonine的首次全合成

First Total Syntheses of 1-Benzoyl-3,4-dihydroisoquinoline Alkaloids Nelumstemine and Longifolonine Based on the Photo-oxidation

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 0

Recommended Articles

Metrics

Comments