Access to the akuammiline family of alkaloids: Total synthesis of (+)-scholarisine A

Journal of the American Chemical Society

Volumn 135, Issue 1, 2013, Pages 519-528

  Adams, Gregory L ^a   Carroll, Patrick J ^a   Smith, Amos B ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVE TOTAL SYNTHESIS; INDOLE RINGS; INDOLIZATION; LACTONIZATION; TOTAL SYNTHESIS;

CHEMICAL COMPOUNDS; CYANIDES; METABOLITES; SCAFFOLDS;

CYCLIZATION;

AKUAMMILINE ALKALOID; ALKALOID; AMINE; EPOXIDE; INDOLE; KETONE; LACTONE; NITRILE; SCHOLARISINE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; LACTONIZATION; OXIDATION;

INDOLE ALKALOIDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84872111353     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3111626     Document Type: Article

References (83)

1. Cai, X. H.; Tan, Q. G.; Liu, Y. P.; Feng, T.; Du, Z. Z.; Li, W. Q.; Luo, X. D. Org. Lett. 2008, 10, 577-580
2. Smith, G. F. Chem. Ind. 1961, 1120
3. Wenkert, E.; Wickberg, B. J. Am. Chem. Soc. 1965, 87, 1580-1589
4. Ramirez, A.; Garcia-Rubio, S. Curr. Med. Chem. 2003, 10, 1891-1915
5. Llopart, C. C.; Joule, J. A. Arkivoc 2004, x, 20-38
6. Rahman, A. U.; Qureshi, M. M.; Ali, S. S. J. Chem. Soc. Pak. 1990, 12, 355-406
7. Olivier, L.; Levy, J.; Le Men, J.; Janot, M. M.; Budzikiewicz, H.; Djerassi, C. Bull. Soc. Chim. Fr. 1965, 868-876
8. Henry, T. A. J. Chem. Soc. 1932, 2759-2768
9. Schnoes, H.; Biemann, K.; Mokry, J.; Kompis, I.; Chatterjee, A.; Ganguli, G. J. Org. Chem. 1966, 31, 1641-1642
10. Ahmad, Y.; Fatima, K.; Rahman, A.; Occolowitz, J.; Solheim, B.; Clardy, J.; Garnick, R.; Le Quesne, P. J. Am. Chem. Soc. 1977, 99, 1943-1946
11. Joule, J. A.; Ohashi, M.; Gilbert, B.; Djerassi, C. Tetrahedron 1965, 21, 1717-1734
12. Ohashi, M.; Joule, J. A.; Djerassi, C. Tetrahedron Lett. 1964, 5, 3899-3905
13. Subramaniam, G.; Hiraku, O.; Hayashi, M.; Koyano, T.; Komiyama, K.; Kam, T. S. J. Nat. Prod. 2007, 70, 1783-1789
14. Zu, L.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 8877-8879
15. Britten, A. Z.; Smith, G. F. J. Chem. Soc. 1963, 3850-3854
16. Britten, A.; Smith, G.; Spiteller, G. Chem. Ind. 1963, 1492-1493
17. Chatterjee, A.; Mukherjee, B.; Ray, A. B.; Das, B. Tetrahedron Lett. 1965, 6, 3633-3637
18. Ghosh, R.; Roychowdhury, P.; Chattopadhyay, D.; Iitaka, Y. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1988, 44, 2151-2154
19. Lewin, G.; Poisson J. Bull. Soc. Chim. Fr. 1980, II-400-II-404
20. Morita, Y.; Hesse, M.; Schmid, H.; Banerji, A.; Banerji, J.; Chatterjee, A.; Oberhansli, W. E. Helv. Chim. Acta 1977, 60, 1419-1434
21. Lim, K. H.; Kam, T. S. Tetrahedron Lett. 2006, 47, 8653-8655
22. Mokry, J.; Dubravkova, L.; Sefcovic, P. Experientia 1962, 18, 564-565
23. Das, B. C.; Cosson, J. P.; Lukacs, G.; Potier, P. Tetrahedron Lett. 1974, 15, 4229-4302
24. Mamatas-Kalamaras, S.; Sevenet, T.; Thal, C.; Potier, P. Phytochemistry 1975, 14, 1637-1639
25. Goodson, J. A.; Henry, T. A. J. Chem. Soc. 1925, 127, 1640-1648
26. Manohar, H.; Ramaseshan, S. Tetrahedron Lett. 1961, 2, 814-816
27. Zhang, M.; Huang, X.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2009, 131, 6013-6020
28. Zi, W.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2012, 134, 9126-9129
29. Arai, H.; Hirasawa, Y.; Rahman, A.; Kusumawati, I.; Zaini, N. C.; Sato, S.; Aoyama, C.; Takeo, J.; Morita, H. Bioorg. Med. Chem. 2010, 18, 2152-2158
30. Meng, W.; Ellsworth, B. A.; Nirschl, A. A.; McCann, P. J.; Patel, M.; Girotra, R. N.; Wu, G.; Sher, P. M.; Morrison, E. P.; Biller, S. A.; Zahler, R.; Deshpande, P. P.; Pullockaran, A.; Hagan, D. L.; Morgan, N.; Taylor, J. R.; Obermeier, M. T.; Humphreys, W. G.; Khanna, A.; Discenza, L.; Robertson, J. G.; Wang, A.; Han, S.; Wetterau, J. R.; Janovitz, E. B.; Flint, O. P.; Whaley, J. M.; Washburn, W. N. J. Med. Chem. 2008, 51, 1145-1149
31. Kamarajan, P.; Sekar, N.; Mathuram, V.; Govindasamy, S. Biochem. Int. 1991, 25, 491-498
32. Jagetia, G. C.; Baliga, M. S.; Venkatesh, P.; Ulloor, J. N.; Mantena, S. K.; Genebriera, J.; Mathuram, V. J. Pharm. Pharmacol. 2005, 57, 1213-1219
33. Adams, G. L.; Carroll, P. J.; Smith, A. B., III J. Am. Chem. Soc. 2012, 134, 4037-4040
34. Laronze, J. Y.; Laronze, J.; Patigny, D.; Levy, J. Terahedron Lett 1986, 27, 489-492
35. Dolby, L. J.; Esfandiari, Z. J. Org. Chem. 1972, 37, 43-46
36. Dolby, L. J.; Nelson, S. J. J. Org. Chem. 1973, 38, 2882-2887
37. For an overview on acid-promoted decomposition of unsaturated α-diazo ketones, see: Smith, A. B., III; Dieter, R. K. Tetrahedron 1981, 37, 2407-2439
38. Bennasar, M. L.; Zulaica, E.; Lopez, M.; Bosch, J. Tetrahedron Lett. 1988, 29, 2361-2364
39. Bosch, J.; Bennasar, M. L. Synlett 1995, 587-596
40. Bennasar, M. L.; Zulaica, E.; Ramirez, A.; Bosch, J. J. Org. Chem. 1996, 61, 1239-1251 Also see refs 24b and 24c.
41. Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. J. Org. Chem. 1995, 60, 2506-2513
42. Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. Tetrahedron 1994, 50, 8837-8852
43. Danieli, B.; Lesma, G.; Mauro, M.; Palmisano, G.; Passarella, D. Tetrahedron: Asymmetry 1990, 1, 793-800
44. Ochiai, H.; Ohtani, T.; Ishida, A.; Kishikawa, K.; Yamamoto, S.; Takeda, H.; Obata, T.; Nakai, H.; Toda, M. Eur. J. Med. Chem. 2004, 39, 555-571
45. Ottolina, G.; Carrea, G.; Riva, S. J. Org. Chem. 1990, 55, 2366-2369
46. Danieli, B.; Lesma, G.; Passarella, D.; Riva, S. Chiral Synthons via Enzyme-Mediated Asymmetrization of Meso -Compounds. In Advances in the Use of Synthons in Organic Chemistry; Dondoni, A., Ed.; JAI Press Inc.: Greenwich, CT, 1993; Vol. 1, pp 143-219.
47. For use of a diamine to quench the reaction of tosyl chloride, see: Morita, J.; Nakatsuji, H.; Misaki, T.; Tanabe, Y. Green Chem. 2005, 7, 711-715
48. Extreme caution should be employed when using potassium cyanide, especially when in a DMSO solution. See: Potassium Cyanide. e-EROS Encyclopedia of Reagents for Organic Synthesis [Online]; Wiley & Sons, Posted April 15, 2001; http://onlinelibrary.wiley.com/o/eros/articles/rp208/frame.html (accessed November 5, 2012).
49. Hughes, T. V.; Hammond, S. D.; Cava, M. P. J. Org. Chem. 1998, 63, 401-402
50. Katritzky, A. R.; Akue-Gedu, R.; Vakulenko, A. V. Arkivoc 2007, iii, 5-12
51. Katritzky, A. R.; Brzezinski, J. Z.; Lam, J. N. Rev. Roum. Chim. 1991, 36, 573-580
52. Kasai, T.; Watanabe, H.; Mori, K. Bioorg. Med. Chem. 1993, 1, 67-70
53. OBrien, P.; Tournayre, J. Tetrahedron 1997, 53, 17527-17542
54. Tarbell, D. S.; West, R. L.; McNally, J. G.; McCorkindale, N. J.; Kunstmann, M.; Carman, R. M.; Cremer, S. E.; Cross, A. D.; Huffman, K. R.; Varino, H. L.; Rosowsky, A.; Chapman, D. D. J. Am. Chem. Soc. 1961, 83, 3096-3113
55. Freifelder, M. J. Am. Chem. Soc. 1960, 82, 2386-2389
56. Schultz, R.; Staas, W.; Spurlock, L. J. Org. Chem. 1973, 38, 3091-3093
57. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156
58. For use of acetic acid as a solvent for nitrile hydrogenation employing rhodium on alumina, see: Galan, A.; De Mendoza, J.; Prados, P.; Rojo, J.; Echavarren, A. M. J. Org. Chem. 1991, 56, 452-454
59. Sajiki, H.; Hattori, K.; Hirota, K. Chem.-Eur. J. 2000, 6, 2200-2204
60. Benzoyl phenylhydrazine has been used in an attempt to avoid pyrazole or pyrazolone formation during Fischer indole syntheses with acyclic 1,3-dicarbonyl compounds. See: Mills, K.; Alkhawaja, K.; Alsaleh, F.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1981, 636-641
61. Welch, W. M. Synthesis 1977, 645-646
62. N -Aroylindoles have been isolated upon Fischer syntheses with aroyl phenylhydrazines. See: Yamamoto, H. J. Org. Chem. 1967, 32, 3693-3695
63. For similar acyl migration, see: Kardos-Balogh, Z.; Soti, F.; Incze, M.; Kajtar-Peredy, M.; Radics, L.; Szantay, C. Heterocycles 1989, 28, 303-312
64. Plieninger, H.; Nogradi, I. Chem. Ber 1955, 88, 1965-1967
65. Chen, F. M. F.; Forrest, T. P. Can. J. Chem. 1973, 51, 881-884
66. Perni, R. B.; Gribble, G. W. Org. Prep. Proced. Int. 1982, 14, 343-346
67. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975-2977
68. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666
69. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1977, 42, 1213-1216
70. Pinchon, T. M.; Nuzillard, J. M.; Richard, B.; Massiot, G.; Le Men-Olivier, L.; Sevenet, T. Phytochemistry 1990, 29, 3341-3344
71. Wang, T.; Xu, Q.; Yu, P.; Liu, X.; Cook, J. M. Org. Lett. 2001, 3, 345-348
72. Yu, J.; Liao, X.; Cook, J. M. Org. Lett. 2002, 4, 4681-4684
73. Parikh, J. R.; Doering, W. E. J. Am. Chem. Soc. 1967, 89, 5505-5507
74. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481-1487
75. N -Methylmorpholine N -oxide is known to oxidize activated halides to the carbonyl oxidation state. See: Griffith, W. P.; Jolliffe, J. M.; Ley, S. V.; Springhorn, K. F.; Tiffin, P. D. Synth. Commun. 1992, 22, 1967-1971
76. Corey, E.; Palani, A. Tetrahedron Lett. 1995, 36, 7945-7948
77. Corey, E.; Palani, A. Tetrahedron Lett. 1995, 36, 3485-3488
78. Watanabe, T.; Kobayashi, A.; Nishiura, M.; Takahashi, H.; Usui, T.; Kamiyama, I.; Mochizuki, N.; Noritake, K.; Yokoyama, Y.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 1152-1156
79. Murakami, Y.; Watanabe, T.; Kobayashi, A.; Yokoyama, Y. Synthesis 1984, 738-740
80. Staab, H.; Walther, G. Chem. Ber. 1962, 95, 2070-2072
81. Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmitt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435-2454
82. Muller, P.; Gilabert, D. Tetrahedron 1988, 44, 7171-7175
83. Larsen, J.; Jorgensen, K. J. Chem. Soc., Perkin Trans. 2 1992, 1213-1217