Biomimetic synthesis of grossularines-1

Angewandte Chemie - International Edition

Volumn 44, Issue 21, 2005, Pages 3280-3282

  Miyake, Fumiko Y ^a   Yakushijin, Kenichi ^a   Horne, David A ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

Alkaloids; Biomimetic synthesis; Dimerization; Natural products; Oxidation

Indexed keywords

AMINES; DIMERIZATION; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALKALOIDS; ANTITUMORS; BIOMIMETIC SYNTHESIS; GROSSULARINES-1;

BIOMIMETIC MATERIALS;

ANTINEOPLASTIC AGENT; BIOMIMETIC MATERIAL; CARBOLINE DERIVATIVE; GROSSULARINE 1; IMIDAZOLE DERIVATIVE; TRYPTAMINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BIOMIMETIC MATERIALS; CARBOLINES; IMIDAZOLES; MOLECULAR STRUCTURE; TRYPTAMINES;

EID: 20344362946     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500055     Document Type: Article

References (20)

1. a) C. Moquin-Pattey, M. Guyot, Tetrahedron 1989, 45, 3445-3450;
2. b) A. Loukaci, M. Guyot, Magn. Reson. Chem. 1996, 34, 143-145;
3. c) N. Helbecque, C. Moquin, J.-L. Bernier, E. Morel, M Guyot, J.-P. Henichart, Cancer Biochem. Biophys. 1987, 9, 271-279.
4. S. A. Abas, M. B. Hossain, D. van der Helm, F. J. Schmitz, M. Laney, R. Cabuslay, R. C. Schatzman, J. Org. Chem. 1996, 61, 2709-2712.
5. T. Choshi, S. Yamada, E. Sugino, T. Kuwada, S. Hibino, J. Org. Chem. 1995, 60, 5899-5904.
6. P. Molina, P. M. Fresneda, M. A. Sanz, C. Foces-Foces, M. C. R. de Arellano, Tetrahedron 1998, 54, 9623-9638.
7. a) F. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2000, 2, 2121-2123;
8. b) F. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2000, 2, 3185-3187;
9. c) F. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2002, 4, 941-943.
10. M. Guyot, M. Meyer, Tetrahedron Lett. 1986, 27, 2621-2622.
11. a) A. Olofson, K. Yakushijin, D. A. Horne, J. Org. Chem. 1998, 63, 1248-1253;
12. b) A. C. Barrios-Sosa, K. Yakushijin, D. A. Horne, J. Org. Chem. 2000, 65, 610-611;
13. c) A. C. Barrios-Sosa, K. Yakushijin, D. A. Horne, J. Org. Chem, 2002, 67, 4498-4500.
14. a) A. Lawson, J. Chem. Soc. 1956, 307-310;
15. b) G. C. Lancini, E. Lazzari, J. Heterocycl. Chem. 1966, 5, 152-166.
16. In contrast to the more commonly observed 2-aminoimidazole unit found in nature, the N,N-dimethylaminoimidazole derivative has been less frequently encountered. For a five-step synthesis of N,N-dimethylaminoimidazole from benzyl isocyanate, see: A. Dalkafouki, J. Ardisson, N. Kunesch, L. Lacombe, J. E. Poisson, Tetrahedron Lett. 1991, 32, 5325-5328.
17. 13C NMR spectra and HRMS analysis.
18. B. R. Lahue, Z.-K. Wan, J. K. Snyder, J. Org. Chem. 2003, 68, 4345-4354.
19. 13C NMR spectral data, to natural and synthetic material reported in references [6] and [9], respectively.
20. For an example of unsymmetrical dimer formation resulting from autoxidation of the indolic neurotoxin 5,6-dihydroxytryptamine, see S. Singh, J.-F. Jen, G. Dryhurst, J. Org. Chem. 1990, 55, 1484-1489.