Volume 44, Issue 21 pp. 3280-3282

Communication

Biomimetic Synthesis of Grossularines-1^†

Fumiko Y. Miyake,

Fumiko Y. Miyake

Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA, Fax: (+1) 541-737-2062

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Kenichi Yakushijin Dr.,

Kenichi Yakushijin Dr.

Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA, Fax: (+1) 541-737-2062

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David A. Horne Dr.,

David A. Horne Dr.

[email protected]

Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA, Fax: (+1) 541-737-2062

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Fumiko Y. Miyake,

Fumiko Y. Miyake

Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA, Fax: (+1) 541-737-2062

Search for more papers by this author

Kenichi Yakushijin Dr.,

Kenichi Yakushijin Dr.

Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA, Fax: (+1) 541-737-2062

Search for more papers by this author

David A. Horne Dr.,

David A. Horne Dr.

[email protected]

Department of Chemistry, Oregon State University, Corvallis, OR 97331, USA, Fax: (+1) 541-737-2062

Search for more papers by this author

First published: 17 May 2005

https://doi.org/10.1002/anie.200500055

Citations: 36

^†

Financial support from the National Institutes of Health (GM71985) and Chugai Pharmaceutical Co. is gratefully acknowledged. We thank Rodger Kohnert for assistance with NMR spectroscopic data acquisition and Jeff Morre of the Mass Spectrometry Facility of the Environmental Health Science Center (NIEHS P30 ES00210) at Oregon State University for recording mass data.

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Graphical Abstract

Like a sea squirt: An efficient biomimetic synthesis of the antitumor α-carboline marine alkaloids grossularine-1 (1) and N,N-didesmethylgrossularine-1 (2) is based on a novel oxidative dimerization of 2-amino-4-(3-indolyl)imidazole.

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References

1
1aC. Moquin-Pattey, M. Guyot, Tetrahedron 1989, 45, 3445–3450;
10.1016/S0040-4020(01)81023-1
CAS Web of Science® Google Scholar
1bA. Loukaci, M. Guyot, Magn. Reson. Chem. 1996, 34, 143–145;
10.1002/(SICI)1097-458X(199602)34:2<143::AID-OMR849>3.0.CO;2-D
CAS Web of Science® Google Scholar
1cN. Helbecque, C. Moquin, J.-L. Bernier, E. Morel, M Guyot, J.-P. Henichart, Cancer Biochem. Biophys. 1987, 9, 271–279.
CAS PubMed Web of Science® Google Scholar
2S. 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.
10.1021/jo960040e
CAS PubMed Web of Science® Google Scholar
3T. Choshi, S. Yamada, E. Sugino, T. Kuwada, S. Hibino, J. Org. Chem. 1995, 60, 5899–5904.
10.1021/jo00123a028
CAS Web of Science® Google Scholar
4P. Molina, P. M. Fresneda, M. A. Sanz, C. Foces-Foces, M. C. R. de Arellano, Tetrahedron 1998, 54, 9623–9638.
10.1016/S0040-4020(98)00520-1
CAS Web of Science® Google Scholar
5
5aF. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2000, 2, 2121–2123;
10.1021/ol000124g
CAS PubMed Web of Science® Google Scholar
5bF. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2000, 2, 3185–3187;
10.1021/ol0001970
CAS PubMed Web of Science® Google Scholar
5cF. Y. Miyake, K. Yakushijin, D. A. Horne, Org. Lett. 2002, 4, 941–943.
10.1021/ol020002j
CAS PubMed Web of Science® Google Scholar
6M. Guyot, M. Meyer, Tetrahedron Lett. 1986, 27, 2621–2622.
10.1016/S0040-4039(00)84600-6
CAS Web of Science® Google Scholar
7
7aA. Olofson, K. Yakushijin, D. A. Horne, J. Org. Chem. 1998, 63, 1248–1253;
10.1021/jo9718298
CAS Web of Science® Google Scholar
7bA. C. Barrios-Sosa, K. Yakushijin, D. A. Horne, J. Org. Chem. 2000, 65, 610–611;
10.1021/jo991277o
CAS PubMed Web of Science® Google Scholar
7cA. C. Barrios-Sosa, K. Yakushijin, D. A. Horne, J. Org. Chem. 2002, 67, 4498–4500.
10.1021/jo020063v
CAS PubMed Web of Science® Google Scholar
8
8aA. Lawson, J. Chem. Soc. 1956, 307–310;
10.1039/JR9560000307
CAS Web of Science® Google Scholar
8bG. C. Lancini, E. Lazzari, J. Heterocycl. Chem. 1966, 3, 152–166.
10.1002/jhet.5570030208
CAS Web of Science® Google Scholar
9In 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.
10.1016/S0040-4039(00)92376-1
CAS Web of Science® Google Scholar
10Structural identity for all new compounds was established on the basis of ¹H and ¹³C NMR spectra and HRMS analysis.
Google Scholar
11B. R. Lahue, Z.-K. Wan, J. K. Snyder, J. Org. Chem. 2003, 68, 4345–4354.
10.1021/jo030049y
CAS PubMed Web of Science® Google Scholar
12Autoxidation of 5⋅HCl took place upon standing in a MeOH solution to yield 2-dimethylamino-5-(3-indolyl)imidazol-4-one (4) as a yellow solid which was identical, by comparison of ¹H and ¹³C NMR spectral data, to natural and synthetic material reported in references [6] and [9], respectively.
Google Scholar
13For 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.
10.1021/jo00292a020
CAS Web of Science® Google Scholar

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Volume44, Issue21

May 20, 2005

Pages 3280-3282

Biomimetic Synthesis of Grossularines-1^†

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Biomimetic Synthesis of Grossularines-1^†