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Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine |
| Yang YANGa,b |
a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b Graduate University of Chinese Academy of Sciences, Beijing 100049, China |
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Abstract We report the first total synthesis of four possible absolute configurations and four other regional isomers of a naturally occurring alkaloid crotonine, which was isolated from Croton tiglium L. (Euphoriaceae) without elucidation of its absolute configuration. The concise five-step route with a chirally poor and regioselective strategy starting from monosaccharides was established, and the absolute structure of the natural crotonine was determined by comparison of the NMR spectra and optical rotations of the synthetic products.
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| Keywords
total synthesis
crotonine
2-(furan-2-yl)-5-(2,3,4-trihydroxy-butyl)-1,4-diazine
Croton tiglium L. (Euphoriaceae)
analgesics
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Issue Date: 11 February 2018
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| [1] |
(a) Mihara, S.; Masuda, H. J. Agric. Food Chem. 1988, 36(6), 1242-1247; (b) Gill, M. S.; Macleod, A. J.; Moreau, M. Phytochemistry 1984, 23(9), 1937-1942.
|
| [2] |
(a) Hwang, H. I.; Hartman, T. G.; Rosen, R. T.; Ho, C. T. J. Agric. Food Chem. 1993, 41(11), 2112-2115; (b) Martin, F. L.; Ames, J. M. J. Agric. Food Chem. 2001, 49(8), 3885-3892.
|
| [3] |
Urban, S.; Hickford, S. J. H.; Blunt, J. W.; Munro, M. H. G. Curr. Org. Chem. 2000, 4(7), 765-807.
|
| [4] |
Cragoe, E. J., Jr.; Woltersdorf, O. W., Jr.; Bicking, J. B.; Kwong, S. F.; Jones, J. H. J. Med. Chem. 1967, 10(1), 66-75.
|
| [5] |
Zhu, A.; Huang, J. B.; Clark, A.; Romero, R.; Petty, H. R. Carbohydr. Res. 2007, 342(18), 2745-2749.
|
| [6] |
Jinsmaa, Y.; Okada, Y.; Tsuda, Y.; Shiotani, K.; Sasaki, Y.; Ambo, A.; Bryant, S. D.; Lazarus, L. H. J. Pharmacol. Exp. Therap. 2004, 309(1), 432-438.
|
| [7] |
Wu, X. A.; Zhao, Y. M.; Yu, N. J. J. Asian Nat. Prod. Res. 2007, 9(5), 437-441.
|
| [8] |
(a) Cho, C. S.; Oh, S. G. Tetrahedron Lett. 2006, 47(32), 5633-5636; (b) Climent, M. J.; Corma, A.; Iborra, S.; MartinezSilvestre, S.; Hernandez, J. C.; Hungria, A. B. J. Catal. 2012, 292, 118-129.
|
| [9] |
Cho, C. S.; Ren, W. X. J. Organomet. Chem. 2009, 694, 3215-3217.
|
| [10] |
Bandyopadhyay, D.; Mukherjee, S.; Rodriguez, R. R.; Banik, B. K. Molecules 2010, 15(6), 4207-4212.
|
| [11] |
(a) El Khadem, H.; Horton, D.; Meshreki, M. H.; Nashed, M. A. Carbohydr. Res. 1970, 13(2), 317-318; (b) Machell, G.; Richards, G. N. J. Chem. Soc. 1960, 1938-1944; (c) Rowell, R. M.; Green, J. Carbohydr. Res. 1970, 15(2), 197-203; (d) El Khadem, H.; Horton, D.; Meshreki, M. H.; Nashed, M. A. Carbohydr. Res. 1971, 17(1), 183-192; (e) El Khadem, H.; Horton, D.; Meshreki, M. H.; Nashed, M. A. Carbohydr. Res. 1972, 22(2), 381-389.
|
| [12] |
O'Donovan, D. H.; Rozas, I. Tetrahedron Lett. 2012, 53(34), 4532-4535.
|
| [13] |
(a) Seko, S.; Komoto, I. J. Chem. Soc., Perkin Trans. 11998, (18), 2975-2976; (b) Seko, S.; Tani, N. Tetrahedron Lett. 1998, 39(44), 8117-8120.
|
| [14] |
Goodwin, H. A.; Lions, F. J. J. Am. Chem. Soc. 1959, 81, 6415.
|
| [15] |
Ghosh, P.; Mandal, A. Green Chem. Lett. Rev. 2012, 5(2), 127-134.
|
| [16] |
Ohta, A.; Watanabe, T.; Akita, Y.; Yoshida, M.; Toda, S.; Akamatsu, T.; Ohno, H.; Suzuki, A. J. Heterocycl. Chem. 1982, 19(5), 1061-1067.
|
| [17] |
(a) Shaaban, M.; Maskey, R. P.; Wagner-Dobler, I.; Laatsch, H. J. Nat. Prod. 2002, 65(11), 1660-1663; (b) Yu, D. Q.; Yang, J. S., The Handbook of Analysis Chemistry, 2nd ed. Chemistry and Industry Publishing House:Beijing:1999.
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