Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine

doi:10.6023/cjoc202204009

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2728-2744.DOI: 10.6023/cjoc202204009 Previous Articles Next Articles

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吲哚生物碱Vindoline与Vindorosine的合成研究进展

孔祥凯^a^,^b, 张逸鹏^a, 党菱婧^c, 陈文^a^,^*(), 张洪彬^a^,^*()

a 云南大学化学科学与工程学院教育部自然资源药物化学重点实验室昆明 650091
b 贵州医科大学贵州省化学合成药物研发利用工程技术研究中心贵阳 550025
c 德宏职业学院医学技术学院云南德宏 678400

收稿日期:2022-04-08 修回日期:2022-05-31 发布日期:2022-06-08
通讯作者: 陈文, 张洪彬
基金资助:
长江学者和创新团队发展计划(IRT17R94); 国家自然科学基金(U1702286); 国家自然科学基金(21762047); 国家自然科学基金(21901224); 云南省基础研究计划(2019FI018); 云南省科技领军人才(202005AB160003); 云南省青年拔尖人才(YNWR-QNBJ-2018-025)

Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine

Xiangkai Kong^a^,^b, Yipeng Zhang^a, Lingjing Dang^c, Wen Chen^a(), Hongbin Zhang^a()

a Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091
b Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang 550025
c School of Medical Technology, Dehong Vocational College, Dehong, Yunnan 678400

Received:2022-04-08 Revised:2022-05-31 Published:2022-06-08
Contact: Wen Chen, Hongbin Zhang
Supported by:
Program for Changjiang Scholars and Innovative Research Team in University(IRT17R94); National Natural Science Foundation of China(U1702286); National Natural Science Foundation of China(21762047); National Natural Science Foundation of China(21901224); Yunnan Fundamental Research Projects(2019FI018); Ling-Jun Scholars of Yunnan Province(202005AB160003); Talent Plan of Yunnan Province(YNWR-QNBJ-2018-025)

Vindoline and vindorosine are two Aspidosperma-type indole alkaloids isolated from the leaves of Catharanthus roseus. Both compounds have highly functionalized pentacyclic indoline skeleton and six contiguous stereogenic centers, three of which are congested quaternary carbon centers. In view of the complex structures of these two molecules and their great challenges in synthesis, 15 research groups have carried out the synthesis of these two molecules. The progress of the synthesis of these two molecules in chronological order is reviewed.

Key words: vindoline, vindorosine, natural product, total synthesis

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Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.

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Fig. & Tab. 21

Figure 1. Several representative compounds of Aspidosperma type alkaloids

Figure 2. Biosynthetic pathway for Vindoline

Scheme 1. Synthesis of (±)-Vindorosine by Büchi's group

Scheme 2. Synthesis of (±)-Vindoline by Büchi's group

Scheme 3. Synthesis by Kutney's group

Scheme 4. Synthesis by Takano's group

Scheme 5. Synthesis by Ban's group

Scheme 6. Synthesis by Palmisano's group

Scheme 7. Synthesis by Langlois' group

Scheme 8. Synthesis by Rapoport's group

Scheme 9. Synthesis by Kuehne's group

Scheme 10. Synthesis by Magnus' group

Scheme 11. Synthesis by Palmisano's group

Scheme 12. Synthesis by Fukuyama's group

Scheme 13. Synthesis by Murphy's group

Scheme 14. First generation synthesis by Boger's group

Scheme 15. Second generation synthesis by Boger's group

Scheme 16. Third generation synthesis by Boger's group

Scheme 17. Synthesis by Hongbin Zhang's group

Scheme 18. Synthesis by Xuefeng Jiang's group

Scheme 19. Synthesis by Maosheng Cheng's group

References 41

[17]	Feldman, P. L.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 1603. doi: 10.1021/ja00239a069
[18]	Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. doi: 10.1021/jo00379a006
[19]	(a) Kuehne, M. E.; Podhorez, D. E. J. Org. Chem. 1985, 50, 924. doi: 10.1021/jo00207a002
	(b) Kuehne, M. E.; Okuniewicz, F. J.; Kirkemo, C. L.; Bohnert, J. C. J. Org. Chem. 1982, 47, 1335. doi: 10.1021/jo00346a034
[20]	(a) Exon, C.; Gallagher, T.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 4739. doi: 10.1021/ja00352a037
	(b) Magnus, P.; Pappalardo, P. A. J. Am. Chem. Soc. 1986, 108, 212. doi: 10.1021/ja00262a005
[21]	Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. doi: 10.1021/ja00215a039
[22]	Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. J. Chem. Soc., Perkin Trans. 1 1987, 155.
[23]	Kobayashi, S.; Peng, G.; Fukuyama, T. Tetrahedron Lett. 1999, 40, 1519. doi: 10.1016/S0040-4039(98)02667-7
[24]	Kobayashi, S.; Ueda, T.; Fukuyama, T. Synlett 2000, 883.
[25]	Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813. doi: 10.1021/ja00237a029
[26]	(a) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, H. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856. doi: 10.1021/jo990891x pmid: 11073654
	(b) Patro, B.; Murphy, J. A. Org. Lett. 2000, 2, 3599. pmid: 11073654
[27]	Zhou, S. Z.; Bommezijn, S.; Murphy, J. A. Org. Lett. 2002, 4, 443. doi: 10.1021/ol0171618
[28]	Elliott, G. I.; Velcicky, J.; Ishikawa, H.; Li, Y. K.; Boger, D. L. Angew. Chem., Int. Ed. 2006, 45, 620.
[29]	(a) Choi, Y. G.; Ishikawa, H.; Velcicky, J.; Elliott, G. I.; Miller, M. M.; Boger, D. L. Org. Lett. 2005, 7, 4539. doi: 10.1021/ol051975x pmid: 16895428
	(b) Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 10596. pmid: 16895428
[1]	Noble, R. L.; Beer, C. T.; Cutts, J. H. Ann. N. Y. Acad. Sci. 1958, 76, 882. doi: 10.1111/j.1749-6632.1958.tb54906.x
[2]	Sears, J. E.; Boger, D. L. Acc. Chem. Res. 2015, 48, 653. doi: 10.1021/ar500400w
[3]	(a) Mascavage, L. M.; Jasmin, S.; Sonnet, P. E.; Wilson, M.; Dalton, D. R. In Ullmann's Encyclopedia of Industrial Chemistry, Vol. 2, Weinheim, 2010, p. 326.
	(b) Saxton, J. E. In The Alkaloids, Vol. 51, Ed.: Cordell, G. A., Academic Press, San Diego, 1998, p. 1.
	(c) Saxton, J. E. In The Alkaloids, Vol. 50, Ed.: Cordell, G. A., Academic Press, San Diego, 1998, p. 343.
	(d) Saya, J. M.; Ruijter, E.; Orru, R. V. A. Chem. Eur. J. 2019, 38, 8916.
	(e) Zhao, S.; Sirasani, G.; Andrade, R. B. In The Alkaloids, Vol. 86, Ed.: Knölker, H.-J., Academic Press, Cambridge, 2021, p. 1.
[4]	(a) Fahn, E.; Lausermair, E.; Deus-Neumann, B.; Stockigt, J. Plant Cell Rep. 1985, 4, 337. doi: 10.1007/BF00269893 pmid: 24254077
	(b) DeLuca, V.; Balsevich, J.; Tyler, R. T.; Eilert, U.; Panchuk, B. D.; Kurz, W. G. W. J. Plant Physiol. 1986, 125, 147. doi: 10.1016/S0176-1617(86)80252-8 pmid: 24254077
	(c) Balsevich, J.; DeLuca, V.; Kurz, W. G. W. Heterocycles 1986, 24, 2415. doi: 10.3987/R-1986-09-2415 pmid: 24254077
[5]	Qu, Y.; Easson, M. L. A. E.; Froese, J.; Simionescu, R.; Hudlicky, T.; De Luca, V. Proc. Natl. Acad. Sci. U. S. A. 2015 112, 6224. doi: 10.1073/pnas.1501821112
[6]	Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. pmid: 5559600
[7]	Ando, M.; Büchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880. doi: 10.1021/ja00856a056
[8]	Kutney, J. P.; Bunzlitrepp, U.; Chan, K. K.; Souza, J. P. D.; Fujise, Y.; Honda, T.; Katsube, J.; Klein, F. K.; Leutwiler, A.; Morehead, S.; Rohr, M.; Worth, B. R. J. Am. Chem. Soc. 1978, 100, 4220. doi: 10.1021/ja00481a035
[9]	(a) Takano, S.; Shishido, K.; Sato, M.; Yuta, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1978, 943.
	(b) Takano, S.; Shishido, K.; Matsuzaka, J. I.; Sato, M.; Ogasawara, K. Heterocycles 1979, 13, 307. doi: 10.3987/S-1979-01-0307
[10]	(a) Dolby, L. J.; Esfandiari, Z. J. Org. Chem. 1972, 37, 43. pmid: 4733444
	(b) Dolby, L. J.; Nelson, S. J. J. Org. Chem. 1973, 38, 2882. pmid: 4733444
[11]	Oishi, M. N. T., Ban, Y. Tetrahedron Lett. 1968, 9, 491. doi: 10.1016/S0040-4039(01)98791-X
[12]	Ban, Y.; Sekine, Y.; Oishi, T. Tetrahedron Lett. 1978, 151.
[13]	Danieli, B.; Lesma, G.; Palmisano, G.; Riva, R. Riva, R. J. Chem. Soc., Chem. Commun. 1984, 909.
[14]	Barton, D. H. R.; Hui, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1982, 1919.
[15]	Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y. J. Chem. Soc., Chem. Commun. 1982, 1118.
[16]	Andriamialisoa, R. Z.; Langlois, N.; Langlois, Y. J. Org. Chem. 1985, 50, 961. doi: 10.1021/jo00207a011
[30]	(a) Kato, D.; Sasaki, Y.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3685. doi: 10.1021/ja910695e
	(b) Sasaki, Y.; Kato, D.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 13533. doi: 10.1021/ja106284s
[31]	(a) Frehel, D.; Badorc, A.; Pereillo, J. M.; Maffrand, J. P. J. Heterocycl. Chem. 1985, 22, 1011. doi: 10.1002/jhet.5570220416
	(b) Kavadias, G.; Velkof, S.; Belleau, B. Can. J. Chem. 1979, 57, 1861. doi: 10.1139/v79-294
[32]	Schleicher, K. D.; Sasaki, Y.; Tam, A.; Kato, D.; Duncan, K. K.; Boger, D. L. J. Med. Chem. 2013, 56, 483. doi: 10.1021/jm3014376 pmid: 23252481
[33]	Sears, J. E.; Barker, T. J.; Boger, D. L. Org. Lett. 2015, 17, 5460. doi: 10.1021/acs.orglett.5b02818
[34]	Sears, J. E.; Boger, D. L. Acc. Chem. Res. 2016, 49, 241. doi: 10.1021/acs.accounts.5b00510
[35]	Chen, W.; Yang, X.-D.; Tan, W.-Y.; Zhang, X.-Y.; Liao, X.-L.; Zhang, H. Angew. Chem., Int. Ed. 2017, 56, 12327. doi: 10.1002/anie.201707249 pmid: 28782228
[36]	Chen, W.; Tian, H.; Tan, W.; Liu, X.; Yang, X.; Zhang, H. Tetrahedron 2019, 75, 1751. doi: 10.1016/j.tet.2018.11.046
[37]	Li, G.; Xu, X.; Tian, H.; Liu, X.; Chen, W.; Yang, X.; Zhang, H. RSC Adv. 2017, 7, 50822. doi: 10.1039/C7RA10529K
[38]	Chen, W.; Ren, J.; Wang, M.; Dang, L.; Shen, X.; Yang, X.; Zhang, H. Chem. Commun. 2014, 50, 6259. doi: 10.1039/C4CC00958D
[39]	Wang, N.; Liu, J.; Wang, C.; Bai, L.; Jiang, X. Org. Lett. 2018, 20, 292. doi: 10.1021/acs.orglett.7b03694
[40]	Bai, L.; Ma, Y.; Jiang, X. J. Am. Chem. Soc. 2021, 143, 20609. doi: 10.1021/jacs.1c10498
[41]	Wang, Y.; Lin, J.; Wang, X.; Wang, G.; Zhang, X.; Yao, B.; Zhao, Y.; Yu, P.; Lin, B.; Liu, Y.; Cheng, M. Chem. Eur. J. 2018, 24, 4026. doi: 10.1002/chem.201705189

吲哚生物碱Vindoline与Vindorosine的合成研究进展

Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine

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Fig. & Tab. 21

References 41

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