Total Synthesis of Hybridaphniphylline B

Journal of the American Chemical Society

Volumn 140, Issue 12, 2018, Pages 4227-4231

  Zhang, Wenhao ^a   Ding, Ming ^a   Li, Jian ^a   Guo, Zhicong ^a   Lu, Ming ^a   Chen, Yu ^a   Liu, Lianchao ^a   Shen, Yun Heng ^b   Li, Ang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; OLEFINS;

CLAISEN REARRANGEMENT; COPE REARRANGEMENT; CYCLOPENTADIENES; DIELS-ALDER REACTION; INTERMOLECULAR DIELS-ALDER REACTIONS; ONE-POT PROTOCOL; PROTIC SOLVENTS; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ALKADIENE; ALKALOID; ASPERULOSIDE TETRAACETATE; CYCLOPENTADIENE DERIVATIVE; DAPHNILONGERANIN B; DAPHNIYUNNINE E; DIENESTROL; GLYCOSIDE; HYBRIDAPHNIPHYLLINE B; NORBORNENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CHEMICAL STRUCTURE; CLAISEN REARRANGEMENT; COPE REARRANGEMENT; CYCLOADDITION; DEACETYLATION; DESULFURIZATION; DIELS ALDER REACTION; EPIMERIZATION; GLYCOSYLATION; LACTONIZATION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TAUTOMERIZATION; X RAY CRYSTALLOGRAPHY;

EID: 85044663137     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.8b01681     Document Type: Article

References (30)

1. Kobayashi, J.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936, 10.1039/b813006j. Chattopadhyay, A. K.; Hanessian, S. Chem. Rev. 2017, 117, 4104, 10.1021/acs.chemrev.6b00412. Kang, B.; Jakubec, P.; Dixon, D. J. Nat. Prod. Rep. 2014, 31, 550, 10.1039/C3NP70115H. Yang, S.-P.; Yue, J.-M. Acta Pharmacol. Sin. 2012, 33, 1147, 10.1038/aps.2012.105
2. For a synthesis of isodaphlongamine H, a presumed Daphniphyllum alkaloid yet to be isolated from nature, see: Chattopadhyay, A. K.; Ly, V. L.; Jakkepally, S.; Berger, G.; Hanessian, S. Angew. Chem., Int. Ed. 2016, 55, 2577, 10.1002/anie.201510861
3. For synthetic studies published after ref (1b), see: Coussanes, G.; Bonjoch, J. Org. Lett. 2017, 19, 878, 10.1021/acs.orglett.7b00035. Shao, H.; Bao, W.; Jing, Z.-R.; Wang, Y.-P.; Zhang, F.-M.; Wang, S.-H.; Tu, Y.-Q. Org. Lett. 2017, 19, 4648, 10.1021/acs.orglett.7b02274
4. Heathcock, C. H.; Davidsen, S. K.; Mills, S.; Sanner, M. A. J. Am. Chem. Soc. 1986, 108, 5650, 10.1021/ja00278a061. Ruggeri, R. B.; Hansen, M. M.; Heathcock, C. H. J. Am. Chem. Soc. 1988, 110, 8734, 10.1021/ja00234a046. Ruggeri, R. B.; McClure, K. F.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 1530, 10.1021/ja00186a075. Ruggeri, R. B.; Heathcock, C. H. J. Org. Chem. 1990, 55, 3714, 10.1021/jo00299a006. Stafford, J. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 5433, 10.1021/jo00307a006. Heathcock, C. H.; Stafford, J. A.; Clark, D. L. J. Org. Chem. 1992, 57, 2575, 10.1021/jo00035a011. Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120, 10.1021/jo00110a013. Piettre, S.; Heathcock, C. H. Science 1990, 248, 1532, 10.1126/science.248.4962.1532
5. Weiss, M. E.; Carreira, E. M. Angew. Chem., Int. Ed. 2011, 50, 11501, 10.1002/anie.201104681
6. Shvartsbart, A.; Smith, A. B., III J. Am. Chem. Soc. 2014, 136, 870, 10.1021/ja411539w. Shvartsbart, A.; Smith, A. B., III J. Am. Chem. Soc. 2015, 137, 3510, 10.1021/ja503899t
7. Yamada, R.; Adachi, Y.; Yokoshima, S.; Fukuyama, T. Angew. Chem., Int. Ed. 2016, 55, 6067, 10.1002/anie.201601958
8. Chen, X.; Zhang, H.-J.; Yang, X.; Lv, H.; Shao, X.; Tao, C.; Wang, H.; Cheng, B.; Li, Y.; Guo, J.; Zhang, J.; Zhai, H. Angew. Chem., Int. Ed. 2018, 57, 947, 10.1002/anie.201709762 In this paper, a synthesis of daphnilongeranin B (4) was reported for the first time.
9. Shi, H.; Michaelides, I. N.; Darses, B.; Jakubec, P.; Nguyen, Q. N. N.; Paton, R. S.; Dixon, D. J. J. Am. Chem. Soc. 2017, 139, 17755, 10.1021/jacs.7b10956
10. Lu, Z.; Li, Y.; Deng, J.; Li, A. Nat. Chem. 2013, 5, 679, 10.1038/nchem.1694. Li, J.; Zhang, W.; Zhang, F.; Chen, Y.; Li, A. J. Am. Chem. Soc. 2017, 139, 14893, 10.1021/jacs.7b09186. Chen, Y.; Zhang, W.; Ren, L.; Li, J.; Li, A. Angew. Chem., Int. Ed. 2018, 57, 952, 10.1002/anie.201711482
11. Li, J.; Yang, P.; Yao, M.; Deng, J.; Li, A. J. Am. Chem. Soc. 2014, 136, 16477, 10.1021/ja5092563. Meng, Z.; Yu, H.; Li, L.; Tao, W.; Chen, H.; Wan, M.; Yang, P.; Edmonds, D. J.; Zhong, J.; Li, A. Nat. Commun. 2015, 6, 6096, 10.1038/ncomms7096. Yang, M.; Li, J.; Li, A. Nat. Commun. 2015, 6, 6445, 10.1038/ncomms7445. Yang, M.; Yang, X.; Sun, H.; Li, A. Angew. Chem., Int. Ed. 2016, 55, 2851, 10.1002/anie.201510568. Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew. Chem., Int. Ed. 2016, 55, 6964, 10.1002/anie.201601915. Li, H.; Chen, Q.; Lu, Z.; Li, A. J. Am. Chem. Soc. 2016, 138, 15555, 10.1021/jacs.6b10880
12. Li, Y.; Zhu, S.; Li, J.; Li, A. J. Am. Chem. Soc. 2016, 138, 3982, 10.1021/jacs.6b00764
13. Wang, F.; Mao, M.-F.; Wei, G.-Z.; Gao, Y.; Ren, F.-C.; Liu, J.-K. Phytochemistry 2013, 95, 428, 10.1016/j.phytochem.2013.07.005
14. For isolation of structurally related alkaloids, see: Di, Y.-T.; Wee, C.-S.; Li, C.-S.; Kong, N.-C.; Wang, J.-S.; Fang, X.; Zhu, H.-J.; Wu, Y.-D.; Hao, X.-J. Tetrahedron 2014, 70, 4017, 10.1016/j.tet.2014.04.073
15. Yang, S.-P.; Zhang, H.; Zhang, C.-R.; Cheng, H.-D.; Yue, J.-M. J. Nat. Prod. 2006, 69, 79, 10.1021/np0503449
16. Zhang, H.; Yang, S.-P.; Fan, C.-Q.; Ding, J.; Yue, J.-M. J. Nat. Prod. 2006, 69, 553, 10.1021/np050490e. Di, Y.-T.; He, H.-P.; Lu, Y.; Yi, P.; Li, L.; Wu, L.; Hao, X.-J. J. Nat. Prod. 2006, 69, 1074, 10.1021/np060088f
17. Zhang, H.; Zhang, D.-D.; Li, J.-Y.; Shyaula, S. L.; Li, J.; Yue, J.-M. RSC Adv. 2016, 6, 44402, 10.1039/C6RA06420E
18. Deng, J.; Zhou, S.; Zhang, W.; Li, J.; Li, R.; Li, A. J. Am. Chem. Soc. 2014, 136, 8185, 10.1021/ja503972p. Deng, J.; Zhu, B.; Lu, Z.; Yu, H.; Li, A. J. Am. Chem. Soc. 2012, 134, 920, 10.1021/ja211444m
19. Spangler, C. W. Chem. Rev. 1976, 76, 187, 10.1021/cr60300a002
20. Sisido, K.; Kurozumi, S.; Utimoto, K. J. Org. Chem. 1969, 34, 2661, 10.1021/jo01261a038
21. Sladojevich, F.; Michaelides, I. N.; Darses, B.; Ward, J. W.; Dixon, D. J. Org. Lett. 2011, 13, 5132, 10.1021/ol202000w
22. Darses, B.; Michaelides, I. N.; Sladojevich, F.; Ward, J. W.; Rzepa, P. R.; Dixon, D. J. Org. Lett. 2012, 14, 1684, 10.1021/ol3002267
23. Xiong, X.; Li, Y.; Lu, Z.; Wan, M.; Deng, J.; Wu, S.; Shao, H.; Li, A. Chem. Commun. 2014, 50, 5294, 10.1039/c3cc47873d
24. Boeckman, R. K., Jr.; del Rosario Rico Ferreira, M.; Mitchell, L. H.; Shao, P. J. Am. Chem. Soc. 2002, 124, 190, 10.1021/ja017194i
25. Grieco, P. A.; Brandes, E. B.; McCann, S.; Clark, J. D. J. Org. Chem. 1989, 54, 5849, 10.1021/jo00286a010
26. Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220, 10.1021/om00025a036
27. Nakatani, K.; Shimano, K.; Hiraishi, A.; Han, Q.; Isoe, S. Bull. Chem. Soc. Jpn. 1993, 66, 2646, 10.1246/bcsj.66.2646
28. Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378, 10.1002/anie.200462207
29. Xiong, X.; Zhang, D.; Li, J.; Sun, Y.; Zhou, S.; Yang, M.; Shao, H.; Li, A. Chem.-Asian J. 2015, 10, 869, 10.1002/asia.201403312
30. Mangion, I. K.; MacMillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3696, 10.1021/ja050064f