Chiral Boron Complex-Promoted Asymmetric Diels-Alder Cycloaddition and Its Application in Natural Product Synthesis

Journal of Organic Chemistry

Volumn 81, Issue 2, 2016, Pages 458-468

  Li, Xia ^a,b   Han, Jianguang ^a,b   Jones, Alexander X ^c   Lei, Xiaoguang ^b,c  

^a TIANJIN UNIVERSITY   (China)

^b NATIONAL INSTITUTE OF BIOLOGICAL SCIENCES   (China)

^c PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORON; BORON COMPOUNDS; ENANTIOSELECTIVITY; OLEFINS;

CYCLOHEXENES; DIASTEREO- AND ENANTIOSELECTIVITY; DIELS-ALDER CYCLOADDITIONS; ENANTIOSELECTIVE CONSTRUCTION; ITS APPLICATIONS; NATURAL PRODUCT SYNTHESIS; NATURAL PRODUCTS; TOTAL SYNTHESIS;

CYCLOADDITION;

ALKADIENE; BORON; BROSIMONE A; BROSIMONE B; CHALCONE DERIVATIVE; CYCLOHEXENE DERIVATIVE; KUWANON I; KUWANON J; METAL COMPLEX; NATURAL PRODUCT; NICOLAIOIDESIN C; PANDURATINE A; UNCLASSIFIED DRUG; 2'-HYDROXYCHALCONE; BIOLOGICAL PRODUCT; BORON DERIVATIVE; CYCLOHEXENE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOSELECTIVITY; STEREOCHEMISTRY; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BIOLOGICAL PRODUCTS; BORON COMPOUNDS; CHALCONES; CYCLOADDITION REACTION; CYCLOHEXENES; STEREOISOMERISM;

EID: 84954415889     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02248     Document Type: Article

References (52)

1. Nomura, T.; Hano, Y. Nat. Prod. Rep. 1994, 11, 205 10.1039/np9941100205
2. Nomura, T. Pure Appl. Chem. 1999, 71, 1115 10.1351/pac199971061115
3. Gu, J. Q.; Park, E. J.; Vigo, J. S.; Graham, J. G.; Fong, H. H.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2002, 65, 1616 10.1021/np020249p
4. Tuntiwachwuttikul, P.; Pancharoen, O.; Reutrakul, V.; Byrne, L. T. Aust. J. Chem. 1984, 37, 449 10.1071/CH9840449
5. Nomura, T.; Fukai, T.; Matsumoto, J.; Ohmori, T. Planta Med. 1982, 46, 167 10.1055/s-2007-970044
6. Ueda, S.; Nomura, T.; Fukai, T.; Massumoto, J. Chem. Pharm. Bull. 1982, 30, 3042 10.1248/cpb.30.3042
7. Messana, I.; Ferrari, F.; De Araujo, M. D. C. M. Tetrahedron 1988, 44, 6693 10.1016/S0040-4020(01)90109-7
8. Messana, I.; Ferrari, F.; de Mello, J. F.; do Carmo Mesquita de Araujo, M. Heterocycles 1989, 29, 683 10.3987/COM-89-4791
9. Nomura, T.; Fukai, T. Chem. Pharm. Bull. 1980, 28, 2548 10.1248/cpb.28.2548
10. Nomura, T.; Fukai, T.; Narita, T. Heterocycles 1980, 14, 1943 10.3987/R-1980-12-1943
11. Deb Majumdar, I.; Devanabanda, A.; Fox, B.; Schwartzman, J.; Cong, H.; Porco, J. A., Jr; Weber, H. C. Biochem. Biophys. Res. Commun. 2011, 416, 397 10.1016/j.bbrc.2011.11.052
12. Kirana, C.; Jones, G. P.; Record, I. R.; McIntosh, G. H. J. Nat. Med. 2007, 61, 131 10.1007/s11418-006-0100-0
13. Cheenpracha, S.; Karalai, C.; Ponglimanont, C.; Subhadhirasakul, S.; Tewtrakul, S. Bioorg. Med. Chem. 2006, 14, 1710 10.1016/j.bmc.2005.10.019
14. Tuchinda, P.; Reutrakul, V.; Claeson, P.; Pongprayoon, U.; Sematong, T.; Santisuk, T.; Taylor, W. C. Phytochemistry 2002, 59, 169 10.1016/S0031-9422(01)00451-4
15. Dai, S. J.; Wu, Y.; Wang, Y. H.; He, W. Y.; Chen, R. Y.; Yu, D. Q. Chem. Pharm. Bull. 2004, 52, 1190 10.1248/cpb.52.1190
16. Zheng, Z. P.; Cheng, K. W.; Zhu, Q.; Wang, X. C.; Lin, Z. X.; Wang, M. J. Agric. Food Chem. 2010, 58, 5368 10.1021/jf1003607
17. see: Han, J.; Jones, A. X.; Lei, X. Synthesis 2015, 47, 1519 10.1055/s-0034-1378696
18. Brito, C. M.; Pinto, D. C. G. A.; Silva, A. M. S.; Silva, A. M. G.; Tome, A. C.; Cavaleiro, J. A. S. Eur. J. Org. Chem. 2006, 2006, 2558 10.1002/ejoc.200500872
19. Jung, E. M.; Lee, Y. R. Bull. Korean Chem. Soc. 2008, 29, 1199 10.5012/bkcs.2008.29.6.1199
20. Chee, C. F.; Abdullah, I.; Buckle, M. J.; Rahman, N. A. Tetrahedron Lett. 2010, 51, 495 10.1016/j.tetlet.2009.11.030
21. Chee, C. F.; Lee, Y. K.; Buckle, M. J. et al. Tetrahedron Lett. 2011, 52, 1797 10.1016/j.tetlet.2011.02.023
22. Gunawan, C.; Rizzacasa, M. A. Org. Lett. 2010, 12, 1388 10.1021/ol9026705
23. Boonsri, S.; Gunawan, C.; Krenske, E. H. Org. Biomol. Chem. 2012, 10, 6010 10.1039/c2ob25115a
24. Cong, H.; Ledbetter, D.; Rowe, G. T.; Caradonna, J. P.; Porco, J. A., Jr. J. Am. Chem. Soc. 2008, 130, 9214 10.1021/ja803094u
25. Cong, H.; Becker, C. F.; Elliott, S. J.; Grinstaff, M. W.; Porco, J. A., Jr. J. Am. Chem. Soc. 2010, 132, 7514 10.1021/ja102482b
26. Cong, H.; Porco, J. A., Jr. Org. Lett. 2012, 14, 2516 10.1021/ol300800r
27. Qi, C.; Cong, H.; Cahill, K. J. Angew. Chem., Int. Ed. 2013, 52, 8345 10.1002/anie.201302847
28. Banuelos, P.; García, J. M.; Gómez-Bengoa, E.; Herrero, A.; Odriozola, J. M.; Oiarbide, M.; Palomo, C.; Razkin, J. J. Org. Chem. 2010, 75, 1458 10.1021/jo9023039
29. Han, J. G.; Li, X.; Guan, Y.; Zhao, W. J.; Wulff, W. D.; Lei, X. G. Angew. Chem., Int. Ed. 2014, 53, 9257 10.1002/anie.201404499
30. Liu, H.; Cun, L. F.; Mi, A. Q.; Jiang, Y. Z.; Gong, L. Z. Org. Lett. 2006, 8, 6023 10.1021/ol062499t
31. Akiyama, T.; Tamura, Y.; Itoh, J.; Morita, H.; Fuchibe, K. Synlett 2006, 2006, 141 10.1055/s-2005-922773
32. Nakashima, D.; Yamamoto, H. J. Am. Chem. Soc. 2006, 128, 9626 10.1021/ja062508t
33. Kelly, T. R.; Whiting, A.; Chandrakumar, N. S. J. Am. Chem. Soc. 1986, 108, 3510 10.1021/ja00272a058
34. Maruoka, K.; Sakurai, M.; Fujiwara, J.; Yamamoto Tetrahedron Lett. 1986, 27, 4895 10.1016/S0040-4039(00)85091-1
35. Wipf, P.; Jung, J. K. J. Org. Chem. 2000, 65, 6319 10.1021/jo000684t
36. Snyder, S. A.; Tang, Z.-Y.; Gupta, R. J. Am. Chem. Soc. 2009, 131, 5744 10.1021/ja9014716
37. Bartoszek, M.; Beller, M.; Deutsch, J.; Klawonn, M.; Köckritz, A.; Nemati, N.; Pews-Davtyan, A. Tetrahedron 2008, 64, 1316 10.1016/j.tet.2007.11.067
38. Bao, J. M.; Wulff, W. D.; Dominy, J. B.; Fumo, M. J.; Grant, E. B.; Rob, A. C.; Whitcomb, M. C.; Yeung, S.-M.; Ostrander, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 3392 10.1021/ja952018t
39. Bao, J. M.; Wulff, W. D. J. Am. Chem. Soc. 1993, 115, 3814 10.1021/ja00062a073
40. Heller, D. P.; Goldberg, D. R.; Wu, H. Q.; Wulff, W. D. Can. J. Chem. 2006, 84, 1487 10.1139/v06-124
41. Matsushita, H.; Negishi, E. J. Org. Chem. 1982, 47, 4161 10.1021/jo00142a031
42. Chou, T.-S.; Tso, H.-H.; Chang, L.-J. J. Chem. Soc., Chem. Commun. 1984, 1323 10.1039/c39840001323
43. Wolinsky, J.; Chollar, B.; Baird, M. D. J. Am. Chem. Soc. 1962, 84, 2775 10.1021/ja00873a027
44. Majetich, G.; Zhang, Y. J. Am. Chem. Soc. 1994, 116, 4979 10.1021/ja00090a050
45. Hano, Y.; Nomura, T.; Ueda, S. J. Chem. Soc., Chem. Commun. 1990, 610 10.1039/c39900000610
46. Helesbeux, J. J.; Duval, O.; Guilet, D.; Seraphin, D.; Rondeau, D.; Richomme, P. Tetrahedron 2003, 59, 5091 10.1016/S0040-4020(03)00733-6
47. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527 10.1038/nchem.687
48. Narayanam, J. M. R.; Stephenson, C. R. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
49. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
50. Hsu, D.-S.; Huang, J.-Y. J. Org. Chem. 2012, 77, 2659-2666 10.1021/jo202448e
51. Roush, W. R.; Sciottir, R. J. J. Am. Chem. Soc. 1998, 120, 7411 10.1021/ja980611f
52. Krohn, K.; Ahmed, I.; John, M. Synthesis 2009, 2009, 779 10.1055/s-0028-1083361