Synthesis of (±)- cis -clavicipitic acid by a Rh(I)-catalyzed intramolecular imine reaction

Journal of Organic Chemistry

Volumn 79, Issue 7, 2014, Pages 3255-3259

  Bartoccini, Francesca ^a   Casoli, Mariangela ^a   Mari, Michele ^a   Piersanti, Giovanni ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ESTERIFICATION; ESTERS; POLYCYCLIC AROMATIC HYDROCARBONS; RHODIUM; SYNTHESIS (CHEMICAL);

FRIEDEL-CRAFTS ALKYLATION; RHODIUM-CATALYZED;

NITROGEN COMPOUNDS;

BORON DERIVATIVE; CLAVICIPITIC ACID; ERGOT ALKALOID; IMINE; INDOLE; INDOLE 4 PINACOLBORONIC ESTER; RHODIUM; UNCLASSIFIED DRUG; BORONIC ACID DERIVATIVE; ESTER; INDOLE DERIVATIVE; INDOLE-4-PINACOLBORONIC ESTER;

ADDITION REACTION; ALKYLATION; ARTICLE; FRIEDEL CRAFTS REACTION; NUCLEOPHILICITY; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALKYLATION; BORONIC ACIDS; CATALYSIS; ERGOT ALKALOIDS; ESTERS; IMINES; INDOLES; MOLECULAR STRUCTURE; RHODIUM; STEREOISOMERISM;

EID: 84898070593     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500245s     Document Type: Article

References (79)

1. Li, S.; Finefield, J. M.; Sunderhaus, J. D.; McAfoos, T. J.; Williams, R. M.; Sherman, D. H. J. Am. Chem. Soc. 2012, 134, 788
2. Lindel, T.; Marsch, N.; Adla, S. K. Top. Curr. Chem. 2012, 309, 67
3. Li, S.-M. Nat. Prod. Rep. 2010, 27, 57
4. Williams, R. M.; Stocking, E. M.; Sanz-Cervera, J. F. Top. Curr. Chem. 2000, 209, 97
5. Robbers, J. E.; Floss, H. G. Tetrahedron Lett. 1969, 10, 1857
6. King, G. S.; Mantle, P. G.; Szczyrbak, C. A.; Waight, E. S. Tetrahedron Lett. 1973, 14, 215
7. King, G. S.; Waight, E. S.; Mantle, P. G.; Szczyrbak, C. A. J. Chem. Soc., Perkin Trans. 1 1977, 2099
8. Robbers, J. E.; Otsuka, H.; Floss, H. G.; Arnold, E. V.; Clardy, J. J. Org. Chem. 1980, 45, 1117
9. Kozlovskii, A. G.; Soloveva, T. F.; Sakharobskii, V. G.; Adanin, V. M. Dokl. Akad. Nauk SSSR 1981, 260, 230
10. Yamada, F.; Makita, Y.; Suzuki, T.; Somei, M. Chem. Pharm. Bull. 1985, 33, 2162
11. Hegedus, L. S.; Toro, J. L.; Miles, W. H.; Harrington, P. J. J. Org. Chem. 1987, 52, 3319
12. Yamada, K.; Namerikawa, Y.; Haruyama, T.; Miwa, Y.; Yanada, R.; Ishikura, M. Eur. J. Org. Chem. 2009, 5752
13. Brak, K.; Ellman, J. A. Org. Lett. 2010, 12, 2004
14. For a nice discussion of indole-based natural products that contain tricyclic benzo[ cd ]indole cores, see: Greshock, T. J.; Funk, R. L. J. Am. Chem. Soc. 2006, 128, 4946
15. May, J. A.; Stoltz, B. M. Tetrahedron 2006, 62, 5262
16. May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44, 1203
17. Krishnan, S.; Bagdanoff, J. T.; Ebner, D. C.; Ramtohul, Y. K.; Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 13745
18. Yokoyama, Y.; Matsumoto, T.; Murakami, Y. J. Org. Chem. 1995, 60, 1486
19. Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Murakami, Y. Tetrahedron Lett. 1999, 40, 7803
20. Yokoyama, Y.; Hikawa, H.; Mitsuhashi, M.; Uyama, A.; Hiroki, Y.; Murakami, Y. Eur. J. Org. Chem. 2004, 1244
21. Shinohara, H.; Fukuda, T.; Iwao, M. Tetrahedron 1999, 55, 10989
22. Ku, J.-M.; Jeong, B.-S.; Jew, S.-s.; Park, H.-g. J. Org. Chem. 2007, 72, 8115
23. Xu, Z.; Li, Q.; Zhang, L.; Jia, Y. J. Org. Chem. 2009, 74, 6859
24. Xu, Z.; Li, Q.; Zhang, L.; Jia, Y. J. Org. Chem. 2010, 75, 6316
25. Xu, Z.; Hu, W.; Liu, Q.; Zhang, L.; Jia, Y. J. Org. Chem. 2010, 75, 7626
26. Liu, Q.; Li, Q.; Ma, Y.; Jia, Y. Org. Lett. 2013, 15, 4528
27. Harrington, P. J.; Hegedus, L. S.; McDaniel, K. F. J. Am. Chem. Soc. 1987, 109, 4335
28. Tian, P.; Dong, H.-Q.; Lin, G.-Q. ACS Catal. 2012, 2, 95
29. Marques, C. S.; Burke, A. J. ChemCatChem 2011, 3, 635
30. Partyka, D. V. Chem. Rev. 2011, 111, 1529
31. Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584
32. Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092
33. Jagt, R. B. C.; Toullec, P. Y.; Geerdink, D.; de Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Angew. Chem., Int. Ed. 2006, 45, 2789
34. Wang, Z.-Q.; Feng, C.-G.; Xu, M.-H.; Lin, G.-Q. J. Am. Chem. Soc. 2007, 129, 5336
35. Trincado, M.; Ellman, J. A. Angew. Chem., Int. Ed. 2008, 47, 5623
36. Cui, Z.; Yu, H.-J.; Yang, R.-F.; Gao, W.-Y.; Feng, C.-G.; Lin, G.-Q J. Am. Chem. Soc. 2011, 133, 12394
37. Ueura, K.; Miyamura, S.; Satoh, T.; Miura, M. J. Organomet. Chem. 2006, 691, 2821
38. Angelini, E.; Balsamini, C.; Bartoccini, F.; Lucarini, S.; Piersanti, G. J. Org. Chem. 2008, 73, 5654
39. Repka, L. M.; Ni, J.; Reisman, S. E. J. Am. Chem. Soc. 2010, 132, 14418
40. Lucarini, S.; Bartoccini, F.; Battistoni, F.; Diamantini, G.; Piersanti, G.; Righi, M.; Spadoni, G. Org. Lett. 2010, 12, 3844
41. Righi, M.; Bartoccini, F.; Lucarini, S.; Piersanti, G. Tetrahedron 2011, 67, 7923
42. Kieffer, M. E.; Repka, L. M.; Reisman, S. E. J. Am. Chem. Soc. 2012, 134, 5131
43. Lucarini, S.; Mari, M.; Piersanti, G.; Spadoni, G. RSC Adv. 2013, 3, 19135
44. Ni, J.; Wang, H.; Reisman, S. E. Tetrahedron 2013, 69, 5622
45. Wang, H.; Ganesan, A. Tetrahedron Lett. 1997, 38, 4327
46. Bailey, P. D.; Cochrane, P. J.; Lorenz, K.; Collier, I. D.; Pearson, D. P. J.; Rosair, G. M. Tetrahedron Lett. 2001, 42, 113
47. Wang, H.; Usui, T.; Osada, H.; Ganesan, A. J. Med. Chem. 2000, 43, 1577
48. Shan, D.; Gao, Y.; Jia, Y. Angew. Chem., Int. Ed. 2013, 52, 4902
49. Park, I.-K.; Park, J.; Cho, C.-G. Angew. Chem., Int. Ed. 2012, 51, 2496
50. Cheng, D.-J.; Wu, H.-B.; Tian, S.-K. Org. Lett. 2011, 13, 5636
51. Schönherr, H.; Leighton, J. L. Org. Lett. 2012, 14, 2610
52. Xu, Q.-L.; Dai, L.-X.; You, S.-L. Chem. Sci. 2013, 4, 97
53. Mari, M.; Bartoccini, F.; Piersanti, G. J. Org. Chem. 2013, 78, 7727
54. Caruana, L.; Fochi, M.; Franchini, M. C.; Ranieri, S.; Mazzanti, A.; Bernardi, L. Chem. Commun. 2014, 50, 445
55. Bartolucci, S.; Bartoccini, F.; Righi, M.; Piersanti, G. Org. Lett. 2012, 14, 600
56. Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583
57. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445
58. Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1998, 120, 11798
59. The Petasis reaction has been reported to be strongly dependent on the solvent. For the best reaction conditions for aryl pinacolboronic esters, see: Jourdan, H.; Gouhier, G.; Van Hijfte, L.; Angibaud, P.; Piettre, S. R. Tetrahedron Lett. 2005, 46, 8027
60. However, the classical Petasis reaction is restricted to activated aldehydes (e.g., glyoxalates) or aldehydes bearing a suitable boron-activating group, typically a free hydroxyl group (e.g., α-hydroxyaldehydes or salicylaldehyde). For a recent comprehensive review, see: Candeias, N. R.; Montalbano, F.; Cal, P. M. S. D.; Gois, P. M. P. Chem. Rev. 2010, 110, 6169 and references therein
61. Liu, G. X.; Lu, X. Y. J. Am. Chem. Soc. 2006, 128, 16504
62. Sarpong, R.; Gallego, G. L Chem. Sci. 2012, 3, 1338
63. Low, D. W.; Pattison, G.; Wieczysty, M. D.; Churchill, G. H.; Lam, H. Org. Lett. 2012, 14, 2548
64. For a nice discussion on the reactivity of arylpalladium(II) species, see: Miura, M.; Nomura, M. Top. Curr. Chem. 2002, 219, 211
65. Tokunaga, N.; Otomaru, Y.; Okamoto, K.; Ueyama, K.; Shintani, R.; Hayashi, T. J. Am. Chem. Soc. 2004, 126, 13584
66. Otomaru, Y.; Tokunaga, N.; Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 307
67. Itooka, R.; Iguchi, Y.; Miyaura, N. Chem. Lett. 2001, 30, 722
68. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052
69. Sakuma, S.; Miyaura, N. J. Org. Chem. 2001, 66, 8944
70. Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000
71. Westermaier, M.; Mayr, H. Org. Lett. 2006, 8, 4791
72. Luk, L. Y. P.; Qian, Q.; Tanner, M. E. J. Am. Chem. Soc. 2011, 133, 12342
73. Schwarzer, D. D.; Gritsch, P. J.; Gaich, T. Angew. Chem., Int. Ed. 2012, 51, 11514
74. Rudolf, J. D.; Wang, H.; Poulter, C. D. J. Am. Chem. Soc. 2013, 135, 1895
75. Liebhold, M.; Li, S.-M. Org. Lett. 2013, 15, 5834-5837
76. Darses, S.; Michaud, G.; Genêt, J.-P. Eur. J. Org. Chem. 1999, 1875
77. Körner, C.; Starkov, P.; Sheppard, T. D. J. Am. Chem. Soc. 2010, 132, 5968
78. Adamczyk-Woźniak, A.; Madura, I.; Velders, A. H.; Sporzyński, A. Tetrahedron Lett. 2010, 51, 6181
79. Tarzia, G.; Balsamini, C.; Spadoni, G.; Duranti, E. Synthesis 1988, 7, 514