Mumford, Peter M., Shiers, Jason J., Tarver, Gary J., Hayes, Jerome F. and Shipman, Michael. (2008) Synthesis of 1,1-disubstituted tetrahydro-beta-carbolines from 2-methyleneaziridines. Tetrahedron Letters, Vol.49 (No.21). pp. 3489-3491. ISSN 00404039

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Abstract

Ring opening of indole functionalised methyleneaziridines (3a-c, 7) with alcohols in the presence of boron trifluoride etherate leads to the formation of 1,1-disubstituted tetrahydro-beta-carbolines in moderate to good yields (37-83%). (c) 2008 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry T Technology > TP Chemical technology
Divisions:	Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH):	Heterocyclic compounds, Ring-opening polymerization, Aziridines
Journal or Publication Title:	Tetrahedron Letters
Publisher:	Pergamon
ISSN:	00404039
Date:	19 May 2008
Volume:	Vol.49
Number:	No.21
Number of Pages:	3
Page Range:	pp. 3489-3491
Identification Number:	10.1016/j.tetlet.2008.03.095
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Engineering and Physical Sciences Research Council (EPSRC), Biotechnology and Biological Sciences Research Council (Great Britain) (BBSRC), Organon (Firm), GlaxoSmithKline
Grant number:	BBSSL-200512206 (BBSRC)
References:	1. Greenhill, J. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon Press: Oxford, 1984; Vol. 4. 2. Kam, T.-S.; Sim, K.-M. Phytochemistry 1998, 47, 145–147. 3. Rabindran, S. K.; Ross, D. D.; Doyle, L. A.; Yang, W.; Greenberger, L. M. Cancer Res. 2000, 60, 47–50. 4. Patil, A. D.; Freyer, A. J.; Carte, B.; Taylor, P. B.; Johnson, R. K.; Faulkner, D. J. J. Nat. Prod. 2002, 65, 628–629. 5. For recent illustrative examples of the use of THBCs in drug discovery, see: (a) Trujillo, J. I.; Meyers, M. J.; Anderson, D. R.; Hegde, S.; Mahoney, M. W.; Vernier, W. F.; Buchler, I. P.; Wu, K. K.; Yang, S.; Hartmann, S. J.; Reitz, D. B. Bioorg. Med. Chem. Lett. 2007, 17, 4657–4663; (b) Chen, C.-H.; Chang, C.-M.; Chen, H.-Y.; Lai, J.-J.; Sun, C.-M. J. Comb. Chem. 2007, 9, 618–626; (c) Diness, F.; Beyer, J.; Meldal, M. Chem. Eur. J. 2006, 12, 8056–8066; (d) Lee, S.-C.; Choi, S. Y.; Chung, Y. K.; Park, S.-B. Tetrahedron Lett. 2006, 47, 6843–6847; (e) Sunder-Plassmann, N.; Sarli, V.; Gartner, M.; Utz, M.; Seiler, J.; Huemmer, S.; Mayer, T. U.; Surrey, T.; Giannis, A. Bioorg. Med. Chem. Lett. 2005, 13, 6094–6111. 6. (a) Daugan, A.; Grondin, P.; Ruault, C.; Le Monnier de Gouville, A.-C.; Coste, H.; Kirilovsky, J.; Hyafil, F.; Labaudinie`re, R. J. Med. Chem. 2003, 46, 4525–4532; (b) Daugan, A.; Grondin, P.; Ruault, C.; Le Monnier de Gouville, A.-C.; Coste, H.; Linget, J.-M.; Kirilovsky, J.; Hyafil, F.; Labaudinie`re, R. J. Med. Chem. 2003, 46, 4533–4542. 7. Herraiz, T.; Galisteo, J.; Chamorro, C. J. Agric. Food Chem. 2003, 51, 2168–2173. 8. For a review, see: Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797– 1842. 9. For alternative strategies to THBCs, see: Bandini, M.; Melloni, A.; Piccinelli, F.; Sinisi, R.; Tommasi, S.; Umani-Ronchi, A. J. Am. Chem. Soc. 2006, 128, 1424–1425 and references cited therein. 10. Lingam, Y.; Rao, D. M.; Bhowmik, D. R.; Santu, P. S.; Rao, K. R.; Islam, A. Tetrahedron Lett. 2007, 48, 7243–7245. 11. Horiguchi, Y.; Nakamura, M.; Kida, A.; Kodama, H.; Saitoh, T.; Sano, T. Heterocycles 2003, 59, 691–705. 12. Shiers, J. J.; Shipman, M.; Hayes, J. F.; Slawin, A. M. Z.; Twin, H. J. Am. Chem. Soc. 2004, 126, 6868–6869 and references cited therein. 13. Prepared by adaption of a recent synthesis of N-benzyltryptamine by: Liu, Y.; Luo, S.; Fu, X.; Fang, F.; Zhuang, Z.; Xiong, W.; Jia, X.; Zhai, H. Org. Lett. 2006, 8, 115–118. 14. Hayes, J. F.; Shipman, M.; Twin, H. J. Org. Chem. 2002, 67, 935–942. 15. Strong NOESY cross-peaks were seen between the Me group at C-1 and H-3, and between the CH2OBn group and the methyl group at C-3. These data are consistent with the depicted (1R*,3R*)- diastereomer.
URI:	http://wrap.warwick.ac.uk/id/eprint/30008

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