Efficient synthesis of 9-aryldihydrophenanthrenes by a cascade reaction involving arynes and styrenes

Organic Letters

Volumn 16, Issue 3, 2014, Pages 676-679

  Bhojgude, Sachin Suresh ^a   Bhunia, Anup ^a   Gonnade, Rajesh G ^a   Biju, Akkattu T ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; PHENANTHRENE DERIVATIVE; STYRENE DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLOADDITION; SYNTHESIS;

CYCLOADDITION REACTION; FLUORIDES; MOLECULAR STRUCTURE; PHENANTHRENES; STYRENES; TRIMETHYLSILYL COMPOUNDS;

EID: 84893867828     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4033094     Document Type: Article

References (60)

1. Wang, X.-Y.; Ke, C.-Q.; Tang, C.-P.; Yuan, D.; Ye, Y. J. Nat. Prod. 2009, 72, 1209
2. Lee, C.-N.; Chang, F.-R.; Yen, M.-H.; Yu, D.; Liu, Y.-N.; Bastow, K. F.; Morris-Natschke, S. L.; Wu, Y.-C.; Lee, K.-H. J. Nat. Prod. 2009, 72, 210
3. Ezaki, K.; Satake, M.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1991, 32, 2793
4. Monache, F. D.; Monache, G. D.; Cavalcanti, J. F.; Pinheiro, R. M. Tetrahedron Lett. 1987, 28, 563
5. For the report on cassigarol C, a 9-aryl 9,10-dihydrophenanthrene natural product, see: Baba, K.; Kido, T.; Taniguchi, M.; Kozawa, M. Phytochemistry 1994, 36, 1509
6. Miles, D. H.; Bhattacharyya, J.; Mody, N. V.; Atwood, J. L.; Black, S.; Hedin, P. A. J. Am. Chem. Soc. 1977, 99, 618
7. Kende, A. S.; Curran, D. P. J. Am. Chem. Soc. 1979, 101, 1857
8. Boger, D. L.; Mitscher, L. A.; Mullican, M. D.; Drake, S. D.; Kitos, P. J. Med. Chem. 1985, 28, 1543
9. Guoa, X.-Y.; Wang, J.; Wang, N.-L.; Kitanaka, S.; Yao, X.-S. J. Asian Nat. Prod. Res. 2007, 9, 165
10. Majumdar, P. L.; Lahiri, S. Phytochemistry 1990, 29, 621
11. Ward, E. W. B.; Unwin, C. H.; Stoessl, A. Can. J. Bot. 1975, 53, 964
12. Fisch, M. H.; Flick, B. H.; Arditti, J. Phytochemistry 1973, 12, 437
13. Suzuki, Y.; Nemoto, T.; Kakugawa, K.; Hamajima, A.; Hamada, Y. Org. Lett. 2012, 14, 2350
14. Ueno, S.; Komiya, S.; Tanaka, T.; Kuwano, R. Org. Lett. 2012, 14, 338
15. Sustac Roman, D.; Takahashi, Y.; Charette, A. B. Org. Lett. 2011, 13, 3242
16. Jana, R.; Chatterjee, I.; Samanta, S.; Ray, J. K. Org. Lett. 2008, 10, 4795
17. Zhu, C.; Shi, Y.; Xu, M.-H.; Lin, G.-Q. Org. Lett. 2008, 10, 1243
18. Pratap, R.; Ram, V. J. J. Org. Chem. 2007, 72, 7402
19. Saito, N.; Shiotani, K.; Kinbara, A.; Sato, Y. Chem. Commun 2009, 4284
20. Bhuvaneswari, S.; Jeganmohan, M.; Cheng, C.-H. Org. Lett. 2006, 8, 5581
21. Quintana, I.; Boersma, A. J.; Peña, D.; Pérez, D.; Guitián, E. Org. Lett. 2006, 8, 3347
22. Hsieh, J.-C.; Rayabarapu, D. K.; Cheng, C.-H. Chem. Commun 2004, 532
23. Pérez, D.; Peña, D.; Guitián, E. Eur. J. Org. Chem. 2013, 5981
24. Wu, C.; Shi, F. Asian J. Org. Chem. 2013, 2, 116
25. Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem. 2013, 11, 191
26. Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112, 3550
27. Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed. 2012, 51, 3766
28. Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev. 2012, 41, 3140
29. Okuma, K. Heterocycles 2012, 85, 515
30. Yoshida, H.; Takaki, K. Synlett 2012, 23, 1725
31. Yoshida, H.; Ohshita, J.; Kunai, A. Bull. Chem. Soc. Jpn. 2010, 83, 199
32. Chen, Y.; Larock, R. C. Arylation Reactions Involving the Formation of Arynes. In Modern Arylation Methods; Ackermann, L., Ed.; Wiley-VCH Verlag: Weinheim, 2009; p 401.
33. Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215
34. Wenk, H. H.; Winkler, M.; Sander, W. Angew. Chem., Int. Ed. 2003, 42, 502
35. Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701
36. Bhojgude, S. S.; Kaicharla, T.; Biju, A. T. Org. Lett. 2013, 15, 5452
37. Bhunia, A.; Porwal, D.; Gonnade, R. G.; Biju, A. T. Org. Lett. 2013, 15, 4620
38. Bhunia, A.; Roy, T.; Pachfule, P.; Rajamohanan, P. R.; Biju, A. T. Angew. Chem., Int. Ed. 2013, 52, 10040
39. Kaicharla, T.; Bhojgude, S. S.; Biju, A. T. Org. Lett. 2012, 14, 6238
40. Bhojgude, S. S.; Kaicharla, T.; Bhunia, A.; Biju, A. T. Org. Lett. 2012, 14, 4098
41. Bhojgude, S. S.; Biju, A. T. Angew. Chem., Int. Ed. 2012, 51, 1520
42. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211
43. Peña, D.; Cobas, A.; Pérez, D.; Guitián, E. Synthesis 2002, 1454
44. Wagner-Jauregg, T. Synthesis 1980, 769
45. Diels, O.; Alder, K. Justus Liebigs Ann. Chem 1926, 450, 237
46. Benedetti, E.; Kocsis, L. S.; Brummond, K. M. J. Am. Chem. Soc. 2012, 134, 12418
47. Kocsis, L. S.; Benedetti, E.; Brummond, K. M. Org. Lett. 2012, 14, 4430
48. Maul, J.; Frushour, B. G.; Kontoff, J. R.; Eichenauer, H.; Ott, K.-H.; Schade, C. Polystyrene and Styrene Copolymers. Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH: Weinheim, 2007; Vol. 29, p 475.
49. Dilling, W. L. Tetrahedron Lett. 1966, 9, 939
50. Davies, W.; Wilmshurst, J. R. J. Chem. Soc 1961, 4079
51. Corbett, T. G.; Porter, Q. N. Aust. J. Chem. 1965, 18, 1781
52. Dyke, S. F.; Marshall, A. R.; Watson, J. P. Tetrahedron 1966, 23, 2515
53. Callander, D. D.; Coe, P. L.; Tatlow, J. C.; Uff, A. J. Tetrahedron 1969, 25, 25
54. Wolthuis, E.; Cady, W. Angew. Chem., Int. Ed. 1967, 6, 555
55. Harrison, R.; Heaney, H.; Jablonski, J. M.; Mason, K. G.; Sketchley, J. M. J. Chem. Soc. C 1969, 1684
56. Dennis, D. A.; Dobrovolsky, D.; Lautens, M. J. Am. Chem. Soc. 2012, 134, 15572
57. Candito, D. A.; Panteleev, J.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 14200
58. Jayanth, T. T.; Jeganmohan, M.; Cheng, M.-J.; Chu, S.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2006, 128, 2232
59. CCDC-960058 (3x) contains 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-request/cif.
60. Bremer, M.; Pauluth, D.; Heckmeier, M.; Diibal, H.-R.; Hornung, B.; Schmidt, W.; Wingen, R. Fluorinated (dihydro) phenanthrene derivatives, and their use in liquid-crystalline media. U.S. Patent 6,495,220, Sep 21, 2004.