Biomimetic approach to communesin B (a.k.a. nomofungin)

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1203-1205

  May, Jeremy A ^a   Zeidan, Ryan K ^a   Stoltz, Brian M ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; AURANTIOCLAVINE; COMMUNESIN B; ERGOT DERIVATIVE; TRYPTAMINE; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; ISOLATION PROCEDURE; MICROFILAMENT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0037415507     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02790-9     Document Type: Article

References (27)

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5. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
6. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
7. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
8. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
9. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
10. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
11. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
12. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
13. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
14. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
15. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
16. 1H NMR data, see Refs. 1, 2, and; (a) Jackson, A. H.; Smith, A. E. J. Chem. Soc. 1964, 5510; (b) Dachriyanus; Sargent, M. V.; Wahyuni, F. S. Aust. J. Chem. 2000, 53, 159; (c) Horne, S.; Taylor, N.; Collins, S.; Rodrigo, R. J. Chem. Soc., Perkin Trans. 1 1991, 3047; (d) Nyerges, M.; Rudas, M.; Bitter, I.; Töke, L. Tetrahedron 1997, 53, 3269; (e) Spande, T. F.; Wilchek, M.; Witkop, B. J. Am. Chem. Soc. 1968, 3256; (f) Chan, T.-L.; Schellenberg, K. A. J. Biol. Chem. 1968, 243, 6284; (g) Decodts, G.; Wakselman, M.; Vilkas, M. Tetrahedron 1970, 26, 3313; (h) Britten, A. Z.; Bardsley, W. G.; Hill, C. M. Tetrahedron 1971, 27, 5631; (i) Lyle, F. R. US Patent 5 973 257, 1985; Chem. Abstr. 1985, 65, 2870; (j) Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303; (k) Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4770; (l) Li, J.; Jeong, S.; Esser, L.; Harran, P. G. Angew. Chem., Int. Ed. 2001, 40, 4765.
17. 13C NMR data, see Refs. 1, 2, 4b, and 4d.
18. 7 A similar tryptamine oxidative dimerization would account for its biogenesis as well.
19. Verbitski S.M., Mayne C.L., Davis R.A., Concepcion G.P., Ireland C.M. J. Org. Chem. 67:2002;7124.
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21. +: 405.1637, found 405.1634.
22. +: 250.1470, found 250.1461.
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24. Iwao M., Motoi O. Tetrahedron Lett. 36:1995;5929.
25. +: 445.2729, found 445.2731.
26. The biosynthetic proposal depicted in Scheme 1 is only one of a number of potential scenarios. Another possibility might involve a combination of the clavicipitic acid/aurantioclavine and chimonanthine biosyntheses. Nonetheless, these routes would also involve two molecules of tryptamine or tryptophan undergoing an oxidative coupling, see; (a) Kirby, G. W.; Shah, S. W.; Herbert, E. J. J. Chem. Soc. C 1969, 1916; (b) Robbers, J. E.; Otsuka, H.; Floss, H. G.; Arnold, E. V.; Clardy, J. J. Org. Chem. 1980, 45, 1117.
27. The biosynthetic proposal depicted in Scheme 1 is only one of a number of potential scenarios. Another possibility might involve a combination of the clavicipitic acid/aurantioclavine and chimonanthine biosyntheses. Nonetheless, these routes would also involve two molecules of tryptamine or tryptophan undergoing an oxidative coupling, see; (a) Kirby, G. W.; Shah, S. W.; Herbert, E. J. J. Chem. Soc. C 1969, 1916; (b) Robbers, J. E.; Otsuka, H.; Floss, H. G.; Arnold, E. V.; Clardy, J. J. Org. Chem. 1980, 45, 1117.