Enantioselective total syntheses of citrinadins A and B. Stereochemical revision of their assigned structures

Journal of the American Chemical Society

Volumn 136, Issue 40, 2014, Pages 14184-14192

  Bian, Zhiguo ^a   Marvin, Christopher C ^a   Pettersson, Martin ^a   Martin, Stephen F ^a  

^a University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; REACTION INTERMEDIATES; STEREOSELECTIVITY;

ABSOLUTE STEREOCHEMISTRY; CONCISE SYNTHESIS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE TOTAL SYNTHESIS; OXIDATIVE REARRANGEMENTS; PYRIDINIUM SALTS; STEREOCHEMICAL STRUCTURES; SUBSTRATE-CONTROLLED REACTIONS;

SYNTHESIS (CHEMICAL);

ALKALOID; CITRINADIN A; CITRINADIN B; UNCLASSIFIED DRUG; INDOLE ALKALOID;

ARTICLE; CHIRALITY; DEOXYGENATION; DRUG STRUCTURE; ENANTIOSELECTIVITY; MANNICH REACTION; RING OPENING; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

CHEMISTRY TECHNIQUES, SYNTHETIC; INDOLE ALKALOIDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84907919625     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja5074646     Document Type: Article

References (71)

1. Bugni, T. S.; Ireland, C. M. Nat. Prod. Rep. 2004, 21, 143-163
2. Saleem, M.; Ali, M. S.; Hussain, S.; Jabbar, A.; Ashraf, M.; Lee, Y. S. Nat. Prod. Rep. 2007, 24, 1142-1152
3. Ratebab, M. E.; Ebel, R. Nat. Prod. Rep. 2011, 28, 290-344
4. Tsuda, M.; Sasaki, M.; Mugishima, T.; Komatsu, K.; Sone, T.; Tanaka, M.; Mikami, Y.; Kobayashi, J. J. Nat. Prod. 2005, 68, 273-276
5. Lu, Z.-Y; Lin, Z.-J.; Wang, W.-L.; Du, L.; Zhu, T.-J.; Fang, Y.-C; Gu, Q.-Q.; Zhu, W.-M. J. Nat. Prod. 2008, 71, 543-546
6. Ueda, J.; Hashimoto, J.; Inaba, S.; Takagi, M.; Shin-ya, K. J. Antibiot. 2010, 63, 203-205
7. Khamthong, N.; Rukachaisirikul, V.; Phongpaichit, S.; Preedanon, S.; Sakayaroj, J. Tetrahedron 2012, 68, 8245-8250
8. El-Neketi, M.; Ebrahim, W.; Lin, W.; Gedara, S.; Badria, F.; Saad, H.-E. A.; Lai, D.; Proksch, P. J. Nat. Prod. 2013, 76, 1099-1104
9. Tsuda, M.; Kasai, Y.; Komatsu, K.; Sone, T.; Tanaka, M.; Mikami, Y.; Kobayashi, J. Org. Lett. 2004, 6, 3087-3089
10. Mugishima, T.; Tsuda, M.; Kasai, Y.; Ishiyama, H.; Fukushi, E.; Kawabata, J.; Watanabe, M.; Akao, K.; Kobayashi, J. J. Org. Chem. 2005, 70, 9430-9435
11. Kushida, N.; Watanabe, N.; Okuda, T.; Yokoyama, F.; Gyobu, Y.; Yaguchi, T. J. Antibiot. 2007, 60, 667-673
12. Pettersson, M.; Knueppel, D.; Martin, S. F. Org. Lett. 2007, 9, 4623-4626
13. McIver, A. L.; Deiters, A. Org. Lett. 2010, 12, 1288-1291
14. Chandler, B. D.; Roland, J. T.; Li, Y.; Sorensen, E. J. Org. Lett. 2010, 12, 2746-2749
15. Guerrero, C. A.; Sorensen, E. J. Org. Lett. 2011, 13, 5164-5167
16. Mundal, D. A.; Sarpong, R. Org. Lett. 2013, 15, 4952-4955
17. Matsumaru, T.; McCallum, M. E.; Enquist, J. A.; Smith, G. M.; Kong, K.; Wood, J. L. Tetrahedron 2014, 70, 4089-4093
18. Kong, K.; Enquist, J. A., Jr.; McCallum, M. E.; Smith, G. M.; Matsumaru, T.; Menhaji-Klotz, E.; Wood, J. L. J. Am. Chem. Soc. 2013, 135, 10890-10893
19. Bian, Z.; Marvin, C. C.; Martin, S. F. J. Am. Chem. Soc. 2013, 135, 10886-10889
20. Smith, A. B., III; Fukui, M.; Vaccaro, H. A.; Empfield, J. R. J. Am. Chem. Soc. 1991, 113, 2071-2092
21. Smith, A. B., III; Empfield, J. R. Chem. Pharm. Bull. 1999, 47, 1671-1678
22. Martin, S. F. Acc. Chem. Res. 2002, 35, 895-904
23. Casiraghi, G.; Battistini, L.; Curti, C.; Rassu, G.; Zanardi, F. Chem. Rev. 2011, 111, 3076-3154
24. Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852
25. Comins, D. L.; Goehring, R. R.; Joseph, S. P.; O'Connor, S. J. Org. Chem. 1990, 55, 2574-2576
26. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719-4728
27. Comins, D. L.; Sahn, J. J. Org. Lett. 2005, 7, 5227-5228
28. For ketalization of 14, see: Shibuya, S.; Isobe, M. Tetrahedron 1998, 54, 6677-6698
29. Zhang, X.; Foote, C. S. J. Am. Chem. Soc. 1993, 115, 8867-8868
30. Adam, W.; Ahrweiler, M.; Peters, K.; Schmiedeskamp, B. J. Org. Chem. 1994, 59, 2733-2739
31. Stevens, R. V. Acc. Chem. Res. 1984, 17, 289-296
32. Neipp, C. E.; Martin, S. F. J. Org. Chem. 2003, 68, 8867-8878
33. Roulland, E.; Cecchin, F.; Husson, H.-P. J. Org. Chem. 2005, 70, 4474-4477
34. Miller, K. A.; Shanahan, C. S.; Martin, S. F. Tetrahedron 2008, 64, 6884-6900
35. Amorde, S. M.; Jewett, I. T.; Martin, S. F. Tetrahedron 2009, 65, 3222-3231
36. Wolckenhauer, S. A.; Rychnovsky, S. D. Tetrahedron 2005, 61, 3371-3381
37. Mukaiyama, T.; Narasaka, K.; Furusato, M. J. Am. Chem. Soc. 1972, 94, 8641-8642
38. Ager, D. J.; East, M. B. J. Org. Chem. 1986, 51, 3983-3992
39. Manas, A.-R. B.; Smith, R. A. J. Chem. Soc., Chem. Commun. 1975, 216-217
40. Cohen, T.; Nolan, S. M. Tetrahedron Lett. 1978, 19, 3533-3536
41. Comins, D. L.; Al-awar, R. S. J. Org. Chem. 1995, 60, 711-716
42. Heitzman, C. L.; Lambert, W. T.; Mertz, E.; Shotwell, J. B.; Tinsley, J. M.; Va, P.; Roush, W. R. Org. Lett. 2005, 7, 2405-2408
43. Robinson, B. Chem. Rev. 1963, 63, 373-401
44. Robinson, B. Chem. Rev. 1969, 69, 227-250
45. Roberson, C. W.; Woerpel, K. A. J. Am. Chem. Soc. 2002, 124, 11342-11348
46. Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209-2219
47. Peterson, A. C.; Cook, J. M. J. Org. Chem. 1995, 60, 120-129
48. Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1996, 118, 557-579
49. Wearing, X. Z.; Cook, J. M. Org. Lett. 2002, 4, 4237-4240
50. Martin, S. F.; Mortimore, M. Tetrahedron Lett. 1990, 31, 4557-4560
51. Martin, S. F.; Benage, B.; Geraci, L. S.; Hunter, J. E.; Mortimore, M. J. Am. Chem. Soc. 1991, 113, 6161-6171
52. Fehr, C. Angew. Chem., Int. Ed. 1998, 37, 2407-2409
53. Carlin, R. B.; Larson, G. W. J. Am. Chem. Soc. 1957, 79, 934-941
54. Chen, J.; Chen, W.; Hu, Y. Synlett 2008, 77-82
55. Greshock, T. J.; Grubbs, A. W.; Tsukamoto, S.; Williams, R. M. Angew. Chem., Int. Ed. 2007, 46, 2262-2265
56. Greshock, T. J.; Grubbs, A. W.; Williams, R. M. Tetrahedron 2007, 63, 6124-6130
57. Greshock, T. J.; Grubbs, A. W.; Jiao, P.; Wicklow, D. T.; Gloer, J. B.; Williams, R. M. Angew. Chem., Int. Ed. 2008, 47, 3573-3577
58. Dutton, J. K.; Steel, R. W.; Tasker, A. S.; Popsavin, V.; Johnson, A. P. J. Chem. Soc., Chem. Commun. 1994, 765-766
59. Cushing, T. D.; Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc. 1996, 118, 557-579
60. Martin, S. F.; Rüeger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6134
61. O'Keefe, B. M.; Simmons, N.; Martin, S. F. Org. Lett. 2008, 10, 5301-5304
62. O'Keefe, B. M.; Simmons, N.; Martin, S. F. Tetrahedron 2011, 67, 4344-4351
63. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470
64. Sonogashira, K. In Contemporary Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 3, pp 521-549.
65. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. 1978, 17, 522-524
66. Lu, B.; Li, C.; Zhang, L. J. Am. Chem. Soc. 2010, 132, 14070-14072
67. Enders, D.; Zhu, J.; Raabe, G. Angew. Chem., Int. Ed. 1996, 35, 1725-1728
68. Hartwig, W. Tetrahedron 1983, 39, 2609-2645
69. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585
70. Pettus, T. R. R.; Inoue, M.; Chen, X.-T.; Danishefsky, S. J. J. Am. Chem. Soc. 2000, 122, 6160-6168
71. Myers, A. G.; Movassaghi, M.; Zheng, B. J. Am. Chem. Soc. 1997, 119, 8572-8573