综述与进展

吲哚生物碱Vindoline与Vindorosine的合成研究进展

  • 孔祥凯 ,
  • 张逸鹏 ,
  • 党菱婧 ,
  • 陈文 ,
  • 张洪彬
展开
  • 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

  网络出版日期: 2022-06-09

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 ,
  • Yipeng Zhang ,
  • Lingjing Dang ,
  • Wen Chen ,
  • Hongbin Zhang
Expand
  • 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
* Corresponding authors. E-mail: ;

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)

摘要

Vindoline与Vindorosine是从长春花中分离得到的Aspidosperma型吲哚生物碱. 两个化合物都具有高度官能团化的五环吲哚啉骨架, 且具有包含3个季碳在内的6个连续的手性中心. 由于这两个分子复杂而有趣的化学结构, 至少有15个课题组对其进行了合成研究. 按照时间顺序对以上两个分子的合成进展进行综述.

本文引用格式

孔祥凯 , 张逸鹏 , 党菱婧 , 陈文 , 张洪彬 . 吲哚生物碱Vindoline与Vindorosine的合成研究进展[J]. 有机化学, 2022 , 42(9) : 2728 -2744 . DOI: 10.6023/cjoc202204009

Abstract

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.

参考文献

[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.
文章导航

/

〈 〉