Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F

Journal of the American Chemical Society

Volumn 138, Issue 24, 2016, Pages 7763-7769

  Lathrop, Stephen P ^a   Pompeo, Matthew ^a   Chang, Wen Tau T ^a   Movassaghi, Mohammad ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ENANTIOSELECTIVITY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CONVERGENT SYNTHESIS; DIASTEREOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; HETERODIMERIZATION; IN- SITU MONITORING; SYNTHESIS FEATURES; TRYPTAMINE DERIVATIVES;

BIOMIMETIC PROCESSES;

ALKALOID DERIVATIVE; COMMUNESIN F; NATURAL PRODUCT; UNCLASSIFIED DRUG; ALKALOID; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; FUSED HETEROCYCLIC RINGS; OXYGEN; RHODIUM; SOLVENT;

ACYLATION; ALLYLATION; AMINATION; ARTICLE; BIOMIMETICS; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; METHANOLYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOPHILICITY; CHEMICAL STRUCTURE; CHEMISTRY; DIMERIZATION; DRUG DESIGN; MATERIALS TESTING; PENICILLIUM; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AMINATION; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; BIOMIMETICS; CATALYSIS; DIMERIZATION; DRUG DESIGN; HETEROCYCLIC COMPOUNDS, 4 OR MORE RINGS; MAGNETIC RESONANCE SPECTROSCOPY; MATERIALS TESTING; MOLECULAR STRUCTURE; OXYGEN; PENICILLIUM; RHODIUM; SOLVENTS; STEREOISOMERISM;

EID: 84976415356     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.6b04072     Document Type: Article

References (74)

1. Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355 10.1016/S0040-4039(00)77612-X
2. Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, P.; Proksch, P. J. Nat. Prod. 2004, 67, 78 10.1021/np030271y
3. Hayashi, H.; Matsumoto, H.; Akiyama, K. Biosci., Biotechnol., Biochem. 2004, 68, 753 10.1271/bbb.68.753
4. Andersen, B.; Smedsgaard, J.; Frisvad, J. C. J. Agric. Food Chem. 2004, 52, 2421 10.1021/jf035406k
5. Dalsgaard, P. W.; Blunt, J. W.; Munro, M. G. H.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 2005, 68, 258 10.1021/np049646l
6. Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124 10.1021/jo026012f
7. For a recent review, see: Trost, B. M.; Osipov, M. Chem.-Eur. J. 2015, 21, 16318 10.1002/chem.201501735
8. Yang, J.; Wu, H.; Shen, Y.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794 10.1021/ja075705g
9. Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem., Int. Ed. 2010, 49, 2000 10.1002/anie.200906818
10. Seo, J. H.; Artman, G. D., III; Weinreb, S. M. J. Org. Chem. 2006, 71, 8891 10.1021/jo061660a
11. Belmar, J.; Funk, R. L. J. Am. Chem. Soc. 2012, 134, 16941 10.1021/ja307277w
12. Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068 10.1021/ja049569g
13. Han, S.-J.; Vogt, F.; Krishnan, S.; May, J. A.; Gatti, M.; Virgil, S. C.; Stoltz, B. M. Org. Lett. 2014, 16, 3316 10.1021/ol5013263
14. Han, S.-J.; Vogt, F.; May, J. A.; Krishnan, S.; Gatti, M.; Virgil, S. C.; Stoltz, B. M. J. Org. Chem. 2015, 80, 528 10.1021/jo502534g
15. Zuo, Z.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2010, 132, 13226 10.1021/ja106739g
16. Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008 10.1002/anie.201106205
17. Movassaghi, M.; Schmidt, M. A. Angew. Chem., Int. Ed. 2007, 46, 3725 10.1002/anie.200700705
18. Schmidt, M. A.; Movassaghi, M. Synlett 2008, 2008, 313 10.1055/s-2008-1032060
19. Kim, J.; Movassaghi, M. Acc. Chem. Res. 2015, 48, 1159 10.1021/ar500454v
20. Woodward, R. B.; Yang, N. C.; Katz, T. J.; Clark, V. M.; Harley-Mason, J.; Ingleby, R. F. J.; Sheppard, N. Proc. Chem. Soc. 1960, 76
21. Robinson, R.; Teuber, H. J. Chem. Ind. 1954, 27, 783
22. Wigley, L. J.; Mantle, P. G.; Perry, D. A. Phytochemistry 2006, 67, 561 10.1016/j.phytochem.2005.10.011
23. May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44, 1203 10.1016/S0040-4039(02)02790-9
24. May, J. A.; Stoltz, B. M. Tetrahedron 2006, 62, 5262 10.1016/j.tet.2006.01.105
25. Cordell, G. A.; Saxton, J. E. In The Alkaloids: Chemistry and Physiology; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 20, pp 3-295.
26. Hino, T.; Nakagawa, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A.; Ed.; Academic Press: New York, 1989; Vol. 34, pp 1-75.
27. Crich, D.; Banerjee, A. Acc. Chem. Res. 2007, 40, 151 10.1021/ar050175j
28. Steven, A.; Overman, L. E. Angew. Chem., Int. Ed. 2007, 46, 5488 10.1002/anie.200700612
29. Xu, J.-B.; Cheng, K.-J. Molecules 2015, 20, 6715 10.3390/molecules20046715
30. Lin, H.-C.; Chiou, G.; Chooi, Y.-H.; McMahon, T. C.; Xu, W.; Garg, N. K.; Tang, Y. Angew. Chem., Int. Ed. 2015, 54, 3004 10.1002/anie.201411297
31. Lin, H.-C.; McMahon, T. C.; Patel, A.; Corsello, M.; Simon, A.; Xu, W.; Zhao, M.; Houk, K. N.; Garg, N. K.; Tang, Y. J. Am. Chem. Soc. 2016, 138, 4002 10.1021/jacs.6b01413
32. Hendrickson, J. B.; Göschke, R.; Rees, R. Tetrahedron 1964, 20, 565 10.1016/S0040-4020(01)98619-3
33. Hall, E. S.; McCapra, F.; Scott, A. I. Tetrahedron 1967, 23, 4131 10.1016/S0040-4020(01)97925-6
34. Guéritte-Voegelein, F.; Sévenet, T.; Pusset, J.; Adeline, M. T.; Gillet, B.; Beloeil, J. C.; Guenard, D.; Potier, P.; Rasolonjanahary, R.; Kordon, C. J. Nat. Prod. 1992, 55, 923 10.1021/np50085a012
35. Lebsack, A. D.; Link, J. T.; Overman, L. E.; Stearns, B. A. J. Am. Chem. Soc. 2002, 124, 9008 10.1021/ja0267425
36. Kozlovskii, A. G.; Soloveva, T. F.; Sakharobskii, V. G.; Adanin, V. M. Dokl. Akad. Nauk SSSR 1981, 260, 230
37. Yamada, F.; Makita, Y.; Suzuki, T.; Somei, M. Chem. Pharm. Bull. 1985, 33, 2162 10.1248/cpb.33.2162
38. Hegedus, L. S.; Toro, J. L.; Miles, W. H.; Harrington, P. J. J. Org. Chem. 1987, 52, 3319 10.1021/jo00391a027
39. Somei, M.; Yamada, F. Heterocycles 2007, 74, 943 10.3987/COM-07-S(W)14
40. Yamada, K.; Namerikawa, Y.; Haruyama, T.; Miwa, Y.; Yanada, R.; Ishikura, M. Eur. J. Org. Chem. 2009, 2009, 5752 10.1002/ejoc.200900742
41. Krishnan, S.; Bagdanoff, J. T.; Ebner, D. C.; Ramtohul, Y. K.; Tambar, U. K.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 13745 10.1021/ja804738b
42. Brak, K.; Ellman, J. A. Org. Lett. 2010, 12, 2004 10.1021/ol100470g
43. Xu, Z. R.; Hu, W. M.; Liu, Q. A.; Zhang, L. H.; Jia, Y. X. J. Org. Chem. 2010, 75, 7626 10.1021/jo101506c
44. Behenna, D. C.; Krishnan, S.; Stoltz, B. M. Tetrahedron Lett. 2011, 52, 2152 10.1016/j.tetlet.2010.11.074
45. Suetsugu, S.; Nishiguchi, H.; Tsukano, C.; Takemoto, Y. Org. Lett. 2014, 16, 996 10.1021/ol4037314
46. Movassaghi, M.; Ahmad, O. K.; Lathrop, S. P. J. Am. Chem. Soc. 2011, 133, 13002 10.1021/ja2057852
47. Lathrop, S. P.; Kim, J.; Movassaghi, M. Chimia 2012, 66, 389 10.2533/chimia.2012.389
48. Lathrop, S. P.; Movassaghi, M. Chem. Sci. 2014, 5, 333 10.1039/C3SC52451E
49. Xie, X.; Jiang, G.; Liu, H.; Hu, J.; Pan, X.; Zhang, H.; Wan, X.; Lai, Y.; Ma, D. Angew. Chem., Int. Ed. 2013, 52, 12924 10.1002/anie.201306774
50. Hoffmann, S.; Seayad, A. M.; List, B. Angew. Chem., Int. Ed. 2005, 44, 7424 10.1002/anie.200503062
51. Kim, J.; Movassaghi, M. J. Am. Chem. Soc. 2011, 133, 14940 10.1021/ja206743v
52. Boyer, N.; Movassaghi, M. Chem. Sci. 2012, 3, 1798 10.1039/c2sc20270k
53. Adams, T. C.; Payette, J. N.; Cheah, J. H.; Movassaghi, M. Org. Lett. 2015, 17, 4268 10.1021/acs.orglett.5b02059
54. Loach, R. P.; Fenton, O. S.; Movassaghi, M. J. Am. Chem. Soc. 2016, 138, 1057 10.1021/jacs.5b12392
55. Roizen, J. L.; Zalatan, D. N.; Du Bois, J. Angew. Chem., Int. Ed. 2013, 52, 11343 10.1002/anie.201304238
56. Benkovics, T.; Guzei, I. A.; Yoon, T. P. Angew. Chem., Int. Ed. 2010, 49, 9153 10.1002/anie.201004635
57. Michaelis, D. J.; Williamson, K. S.; Yoon, T. P. Tetrahedron 2009, 65, 5118 10.1016/j.tet.2009.03.012
58. DePorter, S. M.; Jacobsen, A. C.; Partridge, K. M.; Williamson, K. S.; Yoon, T. P. Tetrahedron Lett. 2010, 51, 5223 10.1016/j.tetlet.2010.08.015
59. Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2010, 132, 4570 10.1021/ja1013536
60. Williamson, K. S.; Yoon, T. P. J. Am. Chem. Soc. 2012, 134, 12370 10.1021/ja3046684
61. Uraguchi, D.; Tsutsumi, R.; Ooi, T. J. Am. Chem. Soc. 2013, 135, 8161 10.1021/ja403491j
62. Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron 1999, 55, 8883 10.1016/S0040-4020(99)00451-2
63. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600 10.1021/cr900382t
64. Davis, F. A.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13 10.1039/a827013z
65. Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003 10.1016/j.tet.2004.06.071
66. Senanayake, C. H.; Krishnamurthy, D.; Lu, Z.-H.; Han, Z.; Gallou, I. Aldrichimica Acta 2005, 38, 93
67. Davis, F. A. J. Org. Chem. 2006, 71, 8993 10.1021/jo061027p
68. Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869 10.1016/j.tet.2006.06.107
69. Herzon, S. B.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 5342 10.1021/ja0510616
70. Overman, L. E.; Jacobsen, E. J. Tetrahedron Lett. 1982, 23, 2741 10.1016/S0040-4039(00)87446-8
71. Ksander, G.; Bold, G.; Lattmann, R.; Lehmann, C.; Fruh, T.; Xiang, Y.-B.; Inomata, K.; Buser, H. P.; Schreiber, J.; Zass, E.; Eschenmoser, A. Helv. Chim. Acta 1987, 70, 1115 10.1002/hlca.19870700424
72. Stork, G. Pure Appl. Chem. 1989, 61, 439 10.1351/pac198961030439
73. Corey, E. J.; Gin, D. Y.; Kania, R. S. J. Am. Chem. Soc. 1996, 118, 9202 10.1021/ja962480t
74. Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828 10.1021/ja993079k