An efficient synthesis of loline alkaloids

Nature Chemistry

Volumn 3, Issue 7, 2011, Pages 543-545

  Cakmak, Mesut ^a   Mayer, Peter ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AZIDE; LOLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; LIMIT OF DETECTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; AZIDES; CRYSTALLOGRAPHY, X-RAY; LIMIT OF DETECTION; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 79959598957     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1072     Document Type: Article

References (27)

1. Trost, B. M. The atom economy-a search for synthetic efficiency. Science 254, 1471-1477(1991). (Pubitemid 21917480)
2. Wender, P. A. & Miller, B. L. Synthesis at the molecular frontier. Nature 460, 197-201(2009).
3. Young, I. S. & Baran, P. S. Protecting-group-free synthesis as an opportunity for invention. Nature Chem. 1, 193-205(2009).
4. Baran, P. S., Maimone, T. J. & Richter, J. M. Total synthesis of marine natural products without using protecting groups. Nature 446, 404-408(2007). (Pubitemid 46476780)
5. Burns, N. Z., Baran, P. S. & Hoffmann, R. W. Redox economy in organic synthesis. Angew. Chem. Int. Ed. 48, 2854-2867(2009).
6. Hofmeister, F. The active constituents of lolium temulentum. Arch. Exp. Pathol. Pharmakol. 30, 203-230(1892).
7. Dannhardt, G. & Steindl, L. Alkaloids of Lolium temulentum-isolation, identification and pharmacological activity. Planta Med. 51, 212-214(1985). (Pubitemid 15000778)
8. Robbins, J. D., Sweeny, J. G., Wilkinson, S. R. & Burdick, D. Volatile alkaloids of Kentucky 31 tall fescue seed (Festuca arundinancea). J. Agric. Food Chem. 20, 1040-1043(1972).
9. Schardl, C. L., Grossman, R. B., Nagabhyru, P., Faulkner, J. R. & Mallik, U. P. Loline alkaloids: currencies of mutualism. Phytochemistry 68, 980-996(2007). (Pubitemid 46415759)
10. Takeda, A., Suzuki, E., Kamei, K. & Nakata, H. Detection and identification of loline and its analogues in horse urine. Chem. Pharm. Bull. 39, 964-968(1991).
11. Batirov, E. K., Malikov, V. M. & Yunusov, S. Y. Lolidine-a new chlorinecontaining alkaloid from the seeds of Lolium cuneatum. Chem. Nat. Prod. 12, 52-54(1977).
12. Magano, J. Synthetic approaches to the neuraminidase inhibitors zanamivir (relenza) and oseltamivir phosphate (Tamiflu) for the treatment of influenza. Chem. Rev. 109, 4398-4438(2009).
13. Olivo, H. F. & Hemenway, M. S. Recent synthesis of epibatidine. A review. Org. Prep. Proced. Int. 34, 1-25(2002).
14. Sakaguchi, H., Tokuyama, H. & Fukuyama, T. Stereocontrolled total synthesis of (2)-kainic acid. Org. Lett. 9, 1635-1638(2007).
15. Glass, R. S., Deardorff, D. R. & Gains, L. H. Pyrrolizidine synthesis by intramolecular cyclization of a substituted azacyclooctane-4, 5-oxide. Tetrahedron Lett. 19, 2965-2968(1978).
16. Wilson, S. R., Sawicki, R. A. & Huffman, J. C. Synthetic and structural studies of the lolium alkaloids. J. Org. Chem. 46, 3887-3891(1981). (Pubitemid 12209167)
17. Tufariello, J. J., Meckler, H. & Winzenberg, K. Synthesis of the lolium alkaloids. J. Org. Chem. 51, 3556-3557(1986).
18. Blakemore, P. R., Schulze, V. K. & White, J. D. Asymmetric synthesis of (+)-loline. Chem. Commun. 1263-1264 (2000). (Pubitemid 30484206)
19. Blakemore, P. R., Kim, S.-K., Schulze, V. K., White, J. D. & Yokochi, A. F. T. Asymmetric synthesis of (+)-loline, a pyrrolizidine alkaloid from rye grass and tall fescue. J. Chem. Soc. Perkin Trans. 1 1831-1845 (2001).
20. Hovey, M. T., Eklund, E. J., Pike, R. D., Mainkar, A. A. & Scheerer, J. R. Synthesis of (+)-acetylnorloline via stereoselective tethered aminohydroxylation. Org. Lett. 13, 1246-1249(2011).
21. Schreiber, S. L., Schreiber, T. S. & Smith, D. B. Reactions that proceed with a combination of enantiotopic group and diastereotopic face selectivity can deliver products with very high enantiomeric excess: experimental support of a mathematical model. J. Am. Chem. Soc. 109, 1525-1529(1987).
22. Smith, D. B., Zhaoyin, W. & Schreiber, S. L. The asymmetric epoxidation of divinyl carbinols: theory and applications. Tetrahedron 46, 4793-4808(1990).
23. Wernerova, M. & Hudlicky, T. On the practical limits of determining isolated product yields and ratios of stereoisomers: reflections, analysis, and redemption. Synlett. 2701-2707 (2010).
24. Wilson, S. R. & Sawicki, R. A. Transannular cyclizations of 1-aza-4-cyclooctene. J. Org. Chem. 44, 287-291(1979).
25. Wilson, S. R. & Sawicki, R. A. The synthesis of hemiloline: 3-aza-9-oxabrendane. Tetrahedron Lett. 19, 2969-2972(1978).
26. Neda, I., Kaukorat, T. & Fischer, A. K. Unusual stabilization of 1, 2-diamino derivatives of quincorine and quincoridine by carbon dioxide: persistent crystalline prim-ammonium-carbamate salts and their reactivity towards isatoic acid anhydride. Eur. J. Org. Chem. 3784-3790 (2003).
27. Jo, E. et al. Crystal structure and electronic properties of 2-amino-2-methyl-1-propanol (AMP) carbamate. Chem. Commun. 46, 9158-9160(2010).