Towards the core structure of strychnos alkaloids using samarium diiodide-induced reactions of indole derivatives

Chemistry - A European Journal

Volumn 19, Issue 52, 2013, Pages 17801-17808

  Beemelmanns, Christine ^a,b   Gross, Steffen ^a,c   Reissig, Hans Ulrich ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b HARVARD MEDICAL SCHOOL   (United States)

^c BASF SE   (Germany)

Author keywords

alkaloids; Barbier reaction; cascade reaction; indole; samarium diiodide

Indexed keywords

BARBIER REACTIONS; CASCADE REACTIONS; CYCLIZATION REACTIONS; FUNCTIONAL GROUP TRANSFORMATIONS; INDOLE; PLAUSIBLE MECHANISMS; SAMARIUM DIIODIDE; TERT-BUTYLDIMETHYLSILYL;

ADDITION REACTIONS; ALKALOIDS; CYCLIZATION; FUNCTIONAL GROUPS; KETONES; METABOLITES; NITROGEN COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS; SYNTHESIS (CHEMICAL);

SAMARIUM;

ALKALOID; INDOLE; INDOLE DERIVATIVE; IODIDE; SAMARIUM; SAMARIUM DIIODIDE;

ARTICLE; BARBIER REACTION; CASCADE REACTION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STRYCHNOS; SYNTHESIS;

ALKALOIDS; BARBIER REACTION; CASCADE REACTION; INDOLE; SAMARIUM DIIODIDE;

ALKALOIDS; CYCLIZATION; INDOLES; IODIDES; MOLECULAR STRUCTURE; SAMARIUM; STRYCHNOS;

EID: 84890989466     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302795     Document Type: Article

References (124)

1. R. J. Sundberg, in The Chemistry of Indoles, Academic, New York, 1970
2. R. J. Sundberg, in Indoles, Academic, London, 1996
3. J. Bonjoch, J. Bosch, in The Alkaloids, Vol.48 (Ed.:, G.A. Cordell,), Academic, San Diego, 1996, 75-189
4. G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075
5. M. Somei, F. Yamada, Nat. Prod. Rep. 2005, 22, 73-103
6. G. R. Humphrey, T. Kuethe, Chem. Rev. 2006, 106, 2875-2911
7. K. Higuchi, T. Kawasaki, Nat. Prod. Rep. 2007, 24, 843-868.
8. S. E. O′Connor, J. J. Maresh, Nat. Prod. Rep. 2006, 23, 532-547
9. S. E. O'Connor, in Comprehensive Natural Products II: Chemistry and Biology, Vol.1 (Eds.,. L. Mander, H.-W. Liu,), Elsevier, 2010, pp. 977-1007
10. W. S. Glenn, W. Runguphan, S. E. O'Connor, Curr. Opin. Biotechnol. 2013, 24, 354-365.
11. R. B. Woodward, M. P. Cava, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker, J. Am. Chem. Soc. 1954, 76, 4749-4751
12. R. B. Woodward, M. P. Cava, W. D. Ollis, A. Hunger, H. U. Daeniker, K. Schenker, Tetrahedron 1963, 19, 247-288.
13. U. Beifuss, Angew. Chem. 1994, 106, 1204-1209
14. Angew. Chem. Int. Ed. Engl. 1994, 33, 1144-1149
15. J. Bonjoch, D. Solé, Chem. Rev. 2000, 100, 3455-3482
16. M. Mori, Heterocycles 2010, 81, 259-292
17. J. S. Cannon, L. E. Overman, Angew. Chem. 2012, 124, 4362-4386
18. Angew. Chem. Int. Ed. 2012, 51, 4288-4311.
19. P. Magnus, M. Giles, R. Bonnert, C. S. Kim, L. McQuire, A. Merritt, N. Vicker, J. Am. Chem. Soc. 1992, 114, 4403-4405
20. S. D. Knight, L. E. Overman, G. Pairaudeau, J. Am. Chem. Soc. 1993, 115, 9293-9294
21. M. E. Kuehne, F. Xu, J. Org. Chem. 1993, 58, 7490-7497
22. V. H. Rawal, S. Iwasa, J. Org. Chem. 1994, 59, 2685-2686
23. M. E. Kuehne, F. Xu, J. Org. Chem. 1998, 63, 9427-9433
24. D. Solé, J. Bonjoch, S. Garcbox drawings light down and leftá-Rubio, E. Peidrõ, J. Bosch, Angew. Chem. 1999, 111, 408-410
25. Angew. Chem. Int. Ed. 1999, 38, 395-397
26. M. Ito, C. W. Clark, M. Mortimore, J. B. Goh, S. F. Martin, J. Am. Chem. Soc. 2001, 123, 8003-8010
27. M. J. Eichberg, R. L. Dorta, K. Lamottke, K. P. C. Vollhardt, Org. Lett. 2000, 2, 2479-2481
28. M. Nakanishi, M. Mori, Angew. Chem. 2002, 114, 2014-2016
29. Angew. Chem. Int. Ed. 2002, 41, 1934-1936
30. T. Ohshima, Y. Xu, R. Takita, S. Shimuzu, D. Zhong, M. Shibasaki, J. Am. Chem. Soc. 2002, 124, 14546-14547
31. Y. Kaburagi, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2004, 126, 10246-10247
32. H. Zhang, J. Boonsombat, A. Padwa, Org. Lett. 2007, 9, 279-282
33. G. Sirasani, T. Paul, W. Dougherty, Jr., S. Kassel, R. B. Andrade, J. Org. Chem. 2010, 75, 3529-3532
34. C. Beemelmanns, H.-U. Reissig, Angew. Chem. 2010, 122, 8195-8199
35. Angew. Chem. Int. Ed. 2010, 49, 8021-8025
36. D. B. C. Martin, C. D. Vanderwal, Chem. Sci. 2011, 2, 649-651
37. S. B. Jones, B. Simmons, A. Mastracchio, D. W. C. MacMillan, Nature 2011, 475, 183-188.
38. G. Stork reported a total synthesis at the Ischia Advanced School of Organic Chemistry, Ischia Porto, Italy, September 21, 1992.
39. Bodwell and Li claimed that a key building block of type I (Figure 2) was obtained in 16 % yield over eight steps starting from tryptamine:, G. J. Bodwell, J. Li, Angew. Chem. 2002, 114, 3395-3396
40. Angew. Chem. Int. Ed. 2002, 41, 3261-3262. However, the relative configuration of this key compound had to be corrected and hence this approach does not constitute a formal total synthesis of strychnine, see ref.[5n].
41. P. J. Parsons, C. S. Penkett, A. J. Shell, Chem. Rev. 1996, 96, 195-206
42. W. Zhang, Curr. Org. Chem. 2004, 8, 757-780
43. G. S. C. Srikanth, S. L. Castle, Tetrahedron 2005, 61, 10377-10441
44. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344
45. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
46. For structure elucidation of vomicin, see:, A. S. Bailey, R. Robinson, Nature 1948, 161, 433-434; for the synthesis of vomicin from strychnine, see
47. P. Rosenmund, M.-P. Schmitt, H. Franke, Liebigs Ann. Chem. 1980, 895-907.
48. For isolation of leucotriene, see:, A. Gan, Y.-Y. Low, T. Etoh, M. Hayashi, K. Komiyama, T.-S. Kam, J. Nat. Prod. 2009, 72, 2098-2103; first total synthesis
49. G. Sirasani, R. B. Andrade, Org. Lett. 2011, 13, 4736-4737.
50. J.-L. Namy, H. B. Kagan, Nouv. J. Chim. 1977, 1, 5-7
51. P. Girard, J.-L. Namy, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693-2698.
52. G. A. Molander, C. R. Harris, Chem. Rev. 1996, 96, 307-338
53. M. Berndt, S. Gross, A. Hölemann, H.-U. Reissig, Synlett 2004, 422-438
54. K. Gopalaiah, H. B. Kagan, New J. Chem. 2008, 32, 607-637
55. D. J. Procter, R. A. Flowers II, T. Skrydstrup, in Organic Synthesis Using Samarium Diiodide, RSC, Cambridge, 2009
56. C. Beemelmanns, H.-U. Reissig, Chem. Soc. Rev. 2011, 40, 2199-2210
57. M. Szostak, M. Spain, D. Parmara, D. J. Procter, Chem. Commun. 2012, 48, 330-346.
58. D. J. Edmonds, D. Johnston, D. J. Procter, Chem. Rev. 2004, 104, 3371-3404
59. K. C. Nicolaou, S. P. Ellery, J. S. Chen, Angew. Chem. 2009, 121, 7276-7301
60. Angew. Chem. Int. Ed. 2009, 48, 7140-7165
61. M. Szostak, D. J. Procter, Angew. Chem. 2011, 123, 7881-7883
62. Angew. Chem. Int. Ed. 2011, 50, 7737-7739.
63. C. U. Dinesh, H.-U. Reissig, Angew. Chem. 1999, 111, 874-876
64. Angew. Chem. Int. Ed. 1999, 38, 789-791
65. E. Nandanan, C. U. Dinesh, H.-U. Reissig, Tetrahedron, 56, 2000, 4267-4277
66. U. K. Wefelscheid, M. Berndt, H.-U. Reissig, Eur. J. Org. Chem. 2008, 3635-3646
67. A. Niermann, J. E. Grössel, H.-U. Reissig, Synlett 2013, 24, 177-180.
68. H.-G. Schmalz, S. Siegel, J. W. Bats, Angew. Chem. 1995, 107, 2597-2599
69. Angew. Chem. Int. Ed. Engl. 1995, 34, 2383-2385
70. J.-S. Shiue, M.-H. Lin, J.-M. Fang, J. Org. Chem. 1997, 62, 4643-4649
71. C.-W. Kuo, J.-M. Fang, Synth. Commun. 2001, 31, 877-892
72. H. Ohno, S. Maeda, M. Okumura, R. Wakayama, T. Tanaka, Chem. Commun. 2002, 316-317
73. H. Ohno, R. Wakayama, S. Maeda, H. Iwasaki, M. Okumura, C. Iwata, H. Mikamiyama, T. Tanaka, J. Org. Chem. 2003, 68, 5909-5916
74. H. Ohno, M. Okumura, S. Maeda, H. Iwasaki, R. Wakayama, T. Tanaka, J. Org. Chem. 2003, 68, 7722-7732.
75. S. Gross, H.-U. Reissig, Org. Lett. 2003, 5, 4305-4307
76. V. Blot, H.-U. Reissig, Eur. J. Org. Chem. 2006, 4989-4992
77. C. Beemelmanns, H.-U. Reissig, Org. Biomol. Chem. 2009, 7, 4475-4480
78. C. Beemelmanns, V. Blot, S. Gross, D. Lentz, H.-U. Reissig, Eur. J. Org. Chem. 2010, 2716-2732
79. C. Beemelmanns, D. Lentz, H.-U. Reissig, Chem. Eur. J. 2011, 17, 9720-9730.
80. J.-S. Shiue, J.-M. Fang, J. Chem. Soc. Chem. Commun. 1993, 1277-1278
81. S.-C. Lin, F.-D. Yang, J.-S. Shiue, S.-M. Yang, J.-M. Fang, J. Org. Chem. 1998, 63, 2909-2917
82. N. Kise, T. Sakurai, Tetrahedron Lett. 2010, 51, 70-74; for a related publication on electrochemical cyclizations of indolyl ketones, see
83. N. Kise, T. Mano, T. Sakurai, Org. Lett. 2008, 10, 4617-4620; for related intermolecular reactions, see
84. N. Kise, A. Sueyoshi, S.-i. Takeuchi, T. Sakurai, Org. Lett. 2013, 15, 2746-2749.
85. H. Wieland, R. G. Jennen, Liebigs Ann. Chem. 1940, 545, 99-112
86. V. Prelog, J. Battegay, W. I. Taylor, Helv. Chim. Acta 1948, 31, 2244-2246.
87. H. Wieland, W. Gumlich, Liebigs Ann. Chem. 1932, 494, 191-200
88. H. Wieland, K. Kaziro, Liebigs Ann. Chem. 1933, 506, 60-76
89. F. A. L. Anet, R. Robinson, J. Chem. Soc. 1955, 2253-2262.
90. G. L. Carroll, R. D. Little, Org. Lett. 2000, 2, 2873-2876
91. G. A. Molander, M. S. Quirmbach, L. F. Silva Jr., K. C. Spencer, J. Balsells, Org. Lett. 2001, 3, 2257-2260
92. J. T. Lowe, J. S. Panek, Org. Lett. 2008, 10, 3813-3816
93. Y. Ito, K. Takahashi, H. Nagase, T. Honda, Org. Lett. 2011, 13, 4640-4643.
94. I. Shinohara, M. Yamada, H. Nagaoka, Tetrahedron Lett. 2003, 44, 4649-4652
95. A. Kishida, H. Nagaoka, Tetrahedron Lett. 2008, 49, 6393-6397.
96. J. Inanaga, M. Ishikawa, M. Yamaguchi, Chem. Lett. 1987, 1485-1486
97. Z. Hou, Y. Wakatsuki, J. Chem. Soc. Chem. Commun. 1994, 1205-1206
98. E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2002, 124, 6895-6899
99. A. Dahlén, G. Hilmersson, Eur. J. Inorg. Chem. 2004, 3393-3403
100. T. Inokuchi, J. Org. Chem. 2005, 70, 1497-1500
101. R. A. Flowers II, Synlett 2008, 1427-1439
102. D. V. Sadasivam, P. K. S. Antharjanam, E. Prasad, R. A. Flowers II, J. Am. Chem. Soc. 2008, 130, 7228-7229
103. H. Farran, S. Hoz, Org. Lett. 2008, 10, 865-867
104. K. A. Choquette, D. V. Sadasivam, R. A. Flowers II, J. Am. Chem. Soc. 2010, 132, 17396-17398
105. D. V. Sadasivam, K. A. Choquette, R. A. Flowers II, J. Vis. Exp. 2013, 72, 4323-4325. For a substitute of carcinogenic HMPA, see
106. C. McDonald, J. D. Ramsey, D. G. Sampsell, J. A. Butler, M. R. Cecchini, Org. Lett. 2010, 12, 5178-5181
107. M. Berndt, A. Hölemann, A. Niermann, C. Bentz, R. Zimmer, H.-U. Reissig, Eur. J. Org. Chem. 2012, 1299-1302.
108. I. Shimizu, T. Yamada, J. Tsuji, Tetrahedron Lett. 1980, 21, 3199-3202
109. T. Tsuda, Y. Chujo, S.-i. Nishi, K. Tawara, T. J. Saegusa, J. Am. Chem. Soc. 1980, 102, 6381-6384
110. E. C. Burger, J. A. Tunge, Org. Lett. 2004, 6, 4113-4115
111. J. T. Mohr, D. C. Behenna, A. W. Harned, B. M. Stoltz, Angew. Chem. 2005, 117, 7084-7087
112. Angew. Chem. Int. Ed. 2005, 44, 6924-6927
113. B. M. Trost, R. N. Bream, J. Xu, Angew. Chem. 2006, 118, 3181-3184
114. Angew. Chem. Int. Ed. 2006, 45, 3109-3112.
115. A. Azzouzi, B. Perrin, M.-E. Sinibaldi, J.-C. Gramain, C. Lavaud, Tetrahedron Lett. 1993, 34, 5451-5454
116. G. A. Kraus, D. Bougie, Tetrahedron 1994, 50, 2681-2690
117. S. H. Tan, M. G. Banwell, A. C. Willis, T. A. Reekie, Org. Lett. 2012, 14, 5621-5623
118. T. A. Reekie, M. G. Banwell, A. C. Willis, J. Org. Chem. 2012, 77, 10773-10781.
119. DFT calculations (GAUSSIAN 09, Rev. A.02/basis set VTZ) by B. Paulus and D. Andrae (Freie Universität Berlin) indicate that a compound such as 25 should have a LUMO energy of about 2.0 eV whereas the simple ketone moiety has a LUMO energy of approximately 3.5 eV. These values indicate that the electron transfer should clearly favor the indole moiety. Nevertheless, these gas phase calculations completely neglect the influence of the solvent and most importantly the highly oxophilic nature of samarium(II). More detailed theoretical studies are in progress and will be reported.
120. A. L. J. Beckwith, Tetrahedron 1981, 37, 3073-3100
121. D. C. Spellmeyer, K. N. Houk, J. Org. Chem. 1987, 52, 959-974.
122. For a review comparing neutral versus radical anions and cations, see:, A. N. Hancock, J. M. Tanko, in Radical Cation/Anion and Neutral Radicals: A Comparison, Encyclopedia of Radicals in Chemistry, Biology and Materials, John, New York, 2012.
123. T. Newhouse, P. S. Baran, R. W. Hoffmann, Chem. Soc. Rev. 2009, 38, 3010-3021
124. R. W. Hoffmann, Russ. J. Org. Chem. 2012, 48, 625-637.