Chinese Journal of Organic Chemistry >
Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine
Received date: 2022-04-08
Revised date: 2022-05-31
Online published: 2022-06-09
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
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 . DOI: 10.6023/cjoc202204009
| [1] | Noble, R. L.; Beer, C. T.; Cutts, J. H. Ann. N. Y. Acad. Sci. 1958, 76, 882. |
| [2] | Sears, J. E.; Boger, D. L. Acc. Chem. Res. 2015, 48, 653. |
| [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. |
| [3] | (b) Saxton, J. E. In The Alkaloids, Vol. 51, Ed.: Cordell, G. A., Academic Press, San Diego, 1998, p. 1. |
| [3] | (c) Saxton, J. E. In The Alkaloids, Vol. 50, Ed.: Cordell, G. A., Academic Press, San Diego, 1998, p. 343. |
| [3] | (d) Saya, J. M.; Ruijter, E.; Orru, R. V. A. Chem. Eur. J. 2019, 38, 8916. |
| [3] | (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. |
| [4] | (b) DeLuca, V.; Balsevich, J.; Tyler, R. T.; Eilert, U.; Panchuk, B. D.; Kurz, W. G. W. J. Plant Physiol. 1986, 125, 147. |
| [4] | (c) Balsevich, J.; DeLuca, V.; Kurz, W. G. W. Heterocycles 1986, 24, 2415. |
| [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. |
| [6] | Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299. |
| [7] | Ando, M.; Büchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880. |
| [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. |
| [9] | (a) Takano, S.; Shishido, K.; Sato, M.; Yuta, K.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1978, 943. |
| [9] | (b) Takano, S.; Shishido, K.; Matsuzaka, J. I.; Sato, M.; Ogasawara, K. Heterocycles 1979, 13, 307. |
| [10] | (a) Dolby, L. J.; Esfandiari, Z. J. Org. Chem. 1972, 37, 43. |
| [10] | (b) Dolby, L. J.; Nelson, S. J. J. Org. Chem. 1973, 38, 2882. |
| [11] | Oishi, M. N. T., Ban, Y. Tetrahedron Lett. 1968, 9, 491. |
| [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. |
| [17] | Feldman, P. L.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 1603. |
| [18] | Kuehne, M. E.; Podhorez, D. E.; Mulamba, T.; Bornmann, W. G. J. Org. Chem. 1987, 52, 347. |
| [19] | (a) Kuehne, M. E.; Podhorez, D. E. J. Org. Chem. 1985, 50, 924. |
| [19] | (b) Kuehne, M. E.; Okuniewicz, F. J.; Kirkemo, C. L.; Bohnert, J. C. J. Org. Chem. 1982, 47, 1335. |
| [20] | (a) Exon, C.; Gallagher, T.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 4739. |
| [20] | (b) Magnus, P.; Pappalardo, P. A. J. Am. Chem. Soc. 1986, 108, 212. |
| [21] | Cardwell, K.; Hewitt, B.; Ladlow, M.; Magnus, P. J. Am. Chem. Soc. 1988, 110, 2242. |
| [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. |
| [24] | Kobayashi, S.; Ueda, T.; Fukuyama, T. Synlett 2000, 883. |
| [25] | Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813. |
| [26] | (a) Kizil, M.; Patro, B.; Callaghan, O.; Murphy, J. A.; Hursthouse, H. B.; Hibbs, D. J. Org. Chem. 1999, 64, 7856. |
| [26] | (b) Patro, B.; Murphy, J. A. Org. Lett. 2000, 2, 3599. |
| [27] | Zhou, S. Z.; Bommezijn, S.; Murphy, J. A. Org. Lett. 2002, 4, 443. |
| [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. |
| [29] | (b) Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 10596. |
| [30] | (a) Kato, D.; Sasaki, Y.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3685. |
| [30] | (b) Sasaki, Y.; Kato, D.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 13533. |
| [31] | (a) Frehel, D.; Badorc, A.; Pereillo, J. M.; Maffrand, J. P. J. Heterocycl. Chem. 1985, 22, 1011. |
| [31] | (b) Kavadias, G.; Velkof, S.; Belleau, B. Can. J. Chem. 1979, 57, 1861. |
| [32] | Schleicher, K. D.; Sasaki, Y.; Tam, A.; Kato, D.; Duncan, K. K.; Boger, D. L. J. Med. Chem. 2013, 56, 483. |
| [33] | Sears, J. E.; Barker, T. J.; Boger, D. L. Org. Lett. 2015, 17, 5460. |
| [34] | Sears, J. E.; Boger, D. L. Acc. Chem. Res. 2016, 49, 241. |
| [35] | Chen, W.; Yang, X.-D.; Tan, W.-Y.; Zhang, X.-Y.; Liao, X.-L.; Zhang, H. Angew. Chem., Int. Ed. 2017, 56, 12327. |
| [36] | Chen, W.; Tian, H.; Tan, W.; Liu, X.; Yang, X.; Zhang, H. Tetrahedron 2019, 75, 1751. |
| [37] | Li, G.; Xu, X.; Tian, H.; Liu, X.; Chen, W.; Yang, X.; Zhang, H. RSC Adv. 2017, 7, 50822. |
| [38] | Chen, W.; Ren, J.; Wang, M.; Dang, L.; Shen, X.; Yang, X.; Zhang, H. Chem. Commun. 2014, 50, 6259. |
| [39] | Wang, N.; Liu, J.; Wang, C.; Bai, L.; Jiang, X. Org. Lett. 2018, 20, 292. |
| [40] | Bai, L.; Ma, Y.; Jiang, X. J. Am. Chem. Soc. 2021, 143, 20609. |
| [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. |
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