Total Synthesis of Loline Alkaloids
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1 Total Synthesis of Loline Alkaloids Cakmak, M.; Mayer, P.; Trauner, D. Nature Chemistry, 2011, 3, Yongzhao Yan Current lit Yongzhao Wipf Group Page 1 of 16 10/12/2014
2 History of Loline Alkaloids First isolated from Lolium temulentum L. in Hofmeister identified a compound with the elemental formula C 7 H 12 N 2 O. 2 Yunusov and Akramov (1966) suggested an endo-nmethyl-1-aminopyrrolizidine structure with a C2 O C7 bridge. 3 Aasen and Culvenor (1969) confirmed this assignment by IR and proton NMR spectroscopy studies. 4 The absolute configuration of loline was finally established by anomalous dispersion X-ray diffraction analysis (Bates and Morehead, 1972) Picture source: Prof. O?o Wilhelm Thomé Flora von Deutschland, Österreich und der Schweiz 1885, Gera, Germany. 2. Hofmeister, F. Arch. Exp. Pathol. Pharmakol , Akramov, S.T.; Yunusov, S.Y. Chem. Nat. Compd , Aasen, A.J.; Culvenor, C.C.J. Aust. J. Chem , Bates, R.B.; Morehead, S.R. Tetrahedron LeK , Yongzhao Wipf Group Page 2 of 16 10/12/2014
3 Members of Loline Alkaloids 2 was isolated Lolium temulentum L. and named norloline. 1,2 N-acetyl norline 3 was found in Festua arundinancea together with some other loline members. 3 4 was the most abundant loline alkaloid. 4 5 was found in urine of horses, which enjoy grazing on tall fescue grass. 4,5 6 was proposed on MS data, but the compound could not be further evaluated due to scarcity of material Hofmeister, F. Arch. Exp. Pathol. Pharmakol , Dannhardt, G.; Steindl, L. Planta Med , Robbins, J. D.; Sweeny, J. G.; Wilkinson, S. R.; Burdick, D. J. Agric. Food Chem , Schardl, C. L.; Grossman, R. B.; Nagabhyru, P.; Faulkner, J. R.; Mallik, U. P. Phytochemistry , Takeda, A.; Suzuki, E.; Kamei, K.; Nakata, H. Chem. Pharm. Bull , Ba]rov, E. K.; Malikov, V. M.; Yunusov, S. Y. Chem. Nat. Prod. 1977, 12, Yongzhao Wipf Group Page 3 of 16 10/12/2014
4 Biological acrvires of Loline Alkaloids Loline alkaloids are produced by endophytic fungi. 1 These alkaloids provided chemoprotection to their host plant. 1 Toxic to insects and aphids but have few negative effects towards mammals. 1 Early studies of loline alkaloid effects on mammalian systems employed crude or partially purified tall fescue extracts that probably had significant amounts of ergot alkaloids. 1 Derivatives of lolines with acyl chain lengths of 8-12 were cytotoxic to tumors and in brine-shrimp assays. 2 Considering the abundance of lolines in some grass-endophyte symbiota, possible additional effects on plant stress and physiology are worth further investigation Schardl, C. L.; Grossman, R. B.; Nagabhyru, P.; Faulkner, J. R.; Mallik, U. P. Phytochemistry , Petroski, R.J.; Powell, R.G.; Sunil, R.; McLaughlin, J.L., Int. J. Pharmacognosy , Yongzhao Wipf Group Page 4 of 16 10/12/2014
5 Biosynthesis of Loline Alkaloids 1. Schardl, C. L.; Grossman, R. B.; Nagabhyru, P.; Faulkner, J. R.; Mallik, U. P. Phytochemistry , Blankenship, J.D.; Houseknecht, J.B.; Pal, S.; Bush, L.P.; Grossman, R.B.; Schardl, C.L. Chembiochem , Faulkner, J.R.; Hussaini, S.R.; Blankenship, J.D.; Pal, S.; Branan, B.M.; Grossman, R.B.; Schardl, C.L. Chembiochem , Yongzhao Wipf Group Page 5 of 16 10/12/2014
6 Previous Synthesis of Loline Alkaloids 1. Glass, R. S.; Deardorff, D. R.; Gains, L. H. Tetrahedron LeK , Yongzhao Wipf Group Page 6 of 16 10/12/2014
7 Previous Synthesis of Loline Alkaloids 1. Wilson, S. R.; Sawicki, R. A.; Huffman, J. C. J. Org. Chem , Yongzhao Wipf Group Page 7 of 16 10/12/2014
8 Previous Synthesis of Loline Alkaloids 1. Tufariello, J. J., Meckler, H., Winzenberg, K. J. Org. Chem , Yongzhao Wipf Group Page 8 of 16 10/12/2014
9 Previous Synthesis of Loline Alkaloids 1. Tufariello, J. J., Meckler, H., Winzenberg, K. J. Org. Chem , Yongzhao Wipf Group Page 9 of 16 10/12/2014
10 Previous Synthesis of Loline Alkaloids 1. Blakemore, P. R.; Schulze, V. K.; White, J. D. Chem. Commun Yongzhao Wipf Group Page 10 of 16 10/12/2014
11 Previous Synthesis of Loline Alkaloids 1. Blakemore, P. R.; Schulze, V. K.; White, J. D. Chem. Commun Yongzhao Wipf Group Page 11 of 16 10/12/2014
12 Previous Synthesis of Loline Alkaloids 1. Hovey, M. T.; Eklund, E. J.; Pike, R. D.; Mainkar, A. A.; Scheerer, J. R. Org. LeK , Yongzhao Wipf Group Page 12 of 16 10/12/2014
13 Previous Synthesis of Loline Alkaloids 1. Hovey, M. T.; Eklund, E. J.; Pike, R. D.; Mainkar, A. A.; Scheerer, J. R. Org. LeK , Yongzhao Wipf Group Page 13 of 16 10/12/2014
14 Efficient Synthesis of Loline Alkaloids 1. Cakmak, M.; Mayer, P.; Trauner, D. Nature Chemistry, 2011, 3, Yongzhao Wipf Group Page 14 of 16 10/12/2014
15 Efficient Synthesis of Loline Alkaloids 1. Cakmak, M.; Mayer, P.; Trauner, D. Nature Chemistry, 2011, 3, Yongzhao Wipf Group Page 15 of 16 10/12/2014
16 Summary 8 steps to build loline skeleton Key transformation is transannular attack of carbamate nitrogen to yield the pyrrolizidine skeleton. Only 1 protecting group is used and lost in course of a strategic bond formation. Scalable, diversifiable and should give access to other members of loline alkaloids. Yongzhao Wipf Group Page 16 of 16 10/12/2014
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