A Highly Efficient Approach to Construct (epi)-Podophyllotoxin-4-O-glycosidic Linkages as well as Its Application in Concise Syntheses of Etoposide and Teniposide

Organic Letters

Volumn 18, Issue 6, 2016, Pages 1294-1297

  Liu, Hui ^a   Liao, Jin Xi ^a   Hu, Yang ^a   Tu, Yuan Hong ^a   Sun, Jian Song ^a  

^a JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ETOPOSIDE; GLYCOSIDE; PODOPHYLLOTOXIN; TENIPOSIDE;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; GLYCOSYLATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CATALYSIS; ETOPOSIDE; GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; PODOPHYLLOTOXIN; TENIPOSIDE;

EID: 84961838048     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00216     Document Type: Article

References (34)

1. Aisner, J.; Whitacre, M. Y.; Budman, D. R.; Propert, K.; Strauss, G.; Van Echo, D. A. V.; Perry, M. Cancer Chemother. Pharmacol. 1992, 29, 435-438 10.1007/BF00684843
2. Price, B. A.; Peters, N. H. Eur. J. Cancer 1992, 28, 615-615 10.1016/S0959-8049(05)80106-6
3. Stadtmauer, E. A.; Cassileth, P. A.; Gale, R. P. Leuk. Res. 1989, 13, 639-650 10.1016/0145-2126(89)90052-0
4. Bostrom, B.; Weisdorf, D. J.; Kim, T.; Kersey, J. H.; Ramsay, N. K. C. Bone Marrow Transplant. 1990, 5, 83-89
5. Kuhn, M.; von Wartburg, A. Helv. Chim. Acta 1968, 51, 163-168 10.1002/hlca.19680510117
6. Kuhn, M.; von Wartburg, A. Helv. Chim. Acta 1968, 51, 1631-1641 10.1002/hlca.19680510719
7. Kuhn, M.; von Wartburg, A. Helv. Chim. Acta 1969, 52, 948-955 10.1002/hlca.19690520411
8. Keller-Juslen, C.; Kuhn, M.; von Wartburg, A. J. Med. Chem. 1971, 14, 936-940 10.1021/jm00292a012
9. Hashimoto, S.-i.; Honda, T.; Ikegami, S. Tetrahedron Lett. 1991, 32, 1653-1654 10.1016/S0040-4039(00)74296-1
10. Allevi, P.; Anastasia, M.; Ciuffreda, P.; Sanvito, A. M.; Macdonald, P. Tetrahedron Lett. 1992, 33, 4831-4834 10.1016/S0040-4039(00)61297-2
11. Allevi, P.; Anastasia, M.; Ciuffreda, P.; Bigatti, E.; Macdonald, P. J. Org. Chem. 1993, 58, 4175-4178 10.1021/jo00067a071
12. Silverberg, L. J.; Kelly, S.; Vemishetti, P.; Vipond, D. H.; Gibson, F. S.; Harrison, B.; Spector, R.; Dillon, J. L. Org. Lett. 2000, 2, 3281-3283 10.1021/ol006262n
13. Berkowitz, D. B.; Choi, S.; Bhuniya, D.; Shoemaker, R. K. Org. Lett. 2000, 2, 1149-1152 10.1021/ol005732a
14. de Jong, R. S.; Slijfer, E. A. M.; Uges, D. R. A.; Mulder, N. H.; de Vries, E. G. E. Br. J. Cancer 1997, 76, 1480-1483 10.1038/bjc.1997.581
15. Rassmann, I.; Thodtmann, R.; Mross, M.; Huttmann, A.; Berdel, W. E.; Manegold, C.; Fiebig, H. H.; Kaeserfrolich, A.; Burk, K.; Hanauske, A. R. Invest. New Drugs 1998, 16, 319-324 10.1023/A:1006293830585
16. Li, Y.; Yang, Y.; Yu, B. Tetrahedron Lett. 2008, 49, 3604-3608 10.1016/j.tetlet.2008.04.017
17. Zhu, Y.; Yu, B. Angew. Chem., Int. Ed. 2011, 50, 8329-8332 10.1002/anie.201103409
18. Tang, Y.; Li, J.; Zhu, Y.; Li, Y.; Yu, B. J. Am. Chem. Soc. 2013, 135, 18396-18405 10.1021/ja4064316
19. Yang, W.; Sun, J.; Lu, W.; Li, Y.; Shan, L.; Han, W.; Zhang, W.-D.; Yu, B. J. Org. Chem. 2010, 75, 6879-6888 10.1021/jo1014189
20. Zhang, Q.; Sun, J.; Zhu, Y.; Zhang, F.; Yu, B. Angew. Chem., Int. Ed. 2011, 50, 4933-4936 10.1002/anie.201100514
21. Yu, J.; Sun, J.; Niu, Y.; Li, R.; Zhang, F.; Yu, B. Chem. Sci. 2013, 4, 3899-3905 10.1039/c3sc51479j
22. Yang, W.; Sun, J.; Yang, Z.; Han, W.; Zhang, W.-D.; Yu, B. Tetrahedron Lett. 2012, 53, 2773-2776 10.1016/j.tetlet.2012.03.103
23. Kamal, A.; Kumar, B. A.; Suresh, P.; Juvekar, A.; Zingde, S. Bioorg. Med. Chem. 2011, 19, 2975-2979 10.1016/j.bmc.2011.03.030
24. Okada, Y.; Asakura, N.; Bando, M.; Ashikaga, Y.; Yamada, H. J. Am. Chem. Soc. 2012, 134, 6940-6943 10.1021/ja301480g
25. Yang, Y.; Li, Y.; Yu, B. J. Am. Chem. Soc. 2009, 131, 12076-12077 10.1021/ja9055245
26. CCDC 143902 (19) and 143901 (20) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data
27. Meng, X.-B.; Yang, L.-D.; Li, H.; Li, Q.; Cheng, T.-M.; Cai, M.-S.; Li, Z.-J. Carbohydr. Res. 2002, 337, 977-981 10.1016/S0008-6215(02)00094-0
28. Zong, G.; Barber, E.; Aljewari, E.; Zhou, J.; Hu, J.; Du, Y. J. Org. Chem. 2015, 80, 9279-9291 10.1021/acs.joc.5b01765
29. Wada, T.; Ohkubo, A.; Mochizuki, A.; Sekine, M. Tetrahedron Lett. 2001, 42, 1069-1072 10.1016/S0040-4039(00)02183-3
30. Love, K. R.; Andrade, R. B.; Seeberger, P. H. J. Org. Chem. 2001, 66, 8165-8176 10.1021/jo015987h
31. Lee, K.-H.; Imakura, Y.; Haruna, M.; Beers, S. A.; Thurston, L. S.; Dai, H.-J.; Chen, C.-H. J. Nat. Prod. 1989, 52, 606-613 10.1021/np50063a021
32. Sum, P.-E.; How, D.; Torres, N.; Petersen, P. J.; Ashcroft, J.; Graziani, E. I.; Koehn, F. E.; Mansour, T. S. Bioorg. Med. Chem. Lett. 2003, 13, 2805-2808 10.1016/S0960-894X(03)00542-0
33. Hoof, S. V.; Ruttens, B.; Hubrecht, I.; Smans, G.; Blom, P.; Sas, B.; Van Hemel, J.; Vandenkerckhove, J.; Van der Eycken, J. Bioorg. Med. Chem. Lett. 2006, 16, 1495-1498 10.1016/j.bmcl.2005.12.048
34. Li, W.; Sha, Y.; Zhu, D. Chin. J. Magn. Reson. 2009, 26, 120-125