Total Synthesis of (- )- Flueggine A And (+)- Virosaine B
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1 Total Synthesis of (- )- Flueggine A And (+)- Virosaine B Yongzhao Yan Current lit Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: Yongzhao Wipf Group Page 1 of 17 2/23/2013
2 (- )- Flueggine A And (+)- Virosaine B Isolated from the twigs and leaves of Flueggea virosa. The structures and absolute configurations of (-)- Flueggine A and (+)-Virosaine B were elucidated by means of NMR, X-ray diffraction and CD analyses. 2,3 (-)-Flueggine A (+)-Virosaine B (-)-Virosaine A 1. Picture source: hbp://blog.roodo.com/ato543/archives/ html 2. B. X. Zhao, Y. Wang, D. M. Zhang, R. W. Jiang, G. C. Wang, J. M. Shi, X. J. Huang, W. M. Chen, C. T. Che, W. C. Ye, Org. LeE. 2011,13, B. X. Zhao, Y. Wang, D. M. Zhang, X. J. Huang, L. L. Bai, Y. Yan, J. M. Chen, T. B. Lu, Y. T. Wang, Q. W. Zhang, W. C. Ye, Org. LeE.2012, 14, Yongzhao Wipf Group Page 2 of 17 2/23/2013
3 Biological AcGviGes Flueggine A exhibited modest activities in three breast cancer cell lines, with IC 50 values of 60±4 (MCF-7), 86±9 (MDA-MB-231), and 68±7 µm (MCF-7/ADR). 1 Flueggine B exhibited a significant inhibitory activity on the growth of MCF-7 and MDA-MB-231 cells, with IC 50 values of 135±5 and 147±3 nm. Neither Virosaine A nor B showed cytotoxic activity against MCF-7, MDA- MB-231, HepG2, HepG2/ADM, HL-60, K562, and Hep2 cells. (-)-Flueggine B (-)-Flueggine A (-)-Virosaine A (+)-Virosaine B 1. B. X. Zhao, Y. Wang, D. M. Zhang, R. W. Jiang, G. C. Wang, J. M. Shi, X. J. Huang, W. M. Chen, C. T. Che, W. C. Ye, Org. LeE. 2011,13, B. X. Zhao, Y. Wang, D. M. Zhang, X. J. Huang, L. L. Bai, Y. Yan, J. M. Chen, T. B. Lu, Y. T. Wang, Q. W. Zhang, W. C. Ye, Org. LeE.2012, 14, Yongzhao Wipf Group Page 3 of 17 2/23/2013
4 Proposed BiosyntheGc Pathways (-)-Flueggine A (-)-norsecurinine (+)-Virosaine B (+)-allonorsecurinine 1. B. X. Zhao, Y. Wang, D. M. Zhang, R. W. Jiang, G. C. Wang, J. M. Shi, X. J. Huang, W. M. Chen, C. T. Che, W. C. Ye, Org. LeE. 2011,13, B. X. Zhao, Y. Wang, D. M. Zhang, X. J. Huang, L. L. Bai, Y. Yan, J. M. Chen, T. B. Lu, Y. T. Wang, Q. W. Zhang, W. C. Ye, Org. LeE.2012, 14, Yongzhao Wipf Group Page 4 of 17 2/23/2013
5 Synthesis of Securinega Alkaloids 1. S. M. Weinreb, Nat. Prod. Rep., 2009, 26, Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: H. Miyatake- Ondozabal, L. M. Bannwart and K. Gademann. Chem. Commun., 2013, 49, 1921 Yongzhao Wipf Group Page 5 of 17 2/23/2013
6 Diels- Alder Routes 1. P. A. Jacobi, C. A. Blum, R. W. DeSimone and U. E. S. Udong, Tetrahedron LeE., 1989, 30, P. A. Jacobi, C. A. Blum, R. W. DeSimone and U. E. S. Udong, J. Org. Chem., 1991, 113, T. Honda, H. Namiki, M. Kudoh, N. Watanabe, H. Nagase and H. Mizutani, Tetrahedron LeE., 2000, 41, T. Honda, H. Namiki, M. Kudoh, H. Nagase and H. Mizutani,Heterocycles, 2003, 59, Yongzhao Wipf Group Page 6 of 17 2/23/2013
7 Weinreb s Synthesis of (- )- norsecurinine 1. G. Han, M. G. LaPorte, J. J. Folmer, K. M. Werner and S. M. Weinreb, Angew. Chem. Int. Ed., 2000, 39, G. Han, M. G. LaPorte, J. J. Folmer, K. M. Werner and S. M. Weinreb, J. Org. Chem., 2000, 65, Yongzhao Wipf Group Page 7 of 17 2/23/2013
8 Vinylogous Mannich ReacGon Route 1. S. Liras, J. E. Davoren and J. Bordner, Org. LeE., 2001, 3, R. Alibes, P. Bayon, P. De March, M. Figueredo, J. Font, E. Garcia- Garcia and D. Gonzalez- Galvez, Org. LeE., 2005, 7, B. M. Trost, R. C. Bunt, R. C. Lemoine and T. L. Calkins, J. Am. Chem. Soc., 2000, 122, Yongzhao Wipf Group Page 8 of 17 2/23/2013
9 Vinylogous Mannich ReacGon Route 1. G. G. Baraji, M. Canto, R. Alibes, P. Bayon, F. Busque, P. De March, M. Figueredo and J. Font, J. Org. Chem., 2008, 73, H. Miyatake- Ondozabal, L. M. Bannwart and K. Gademann. Chem. Commun., 2013, 49, 1921 Yongzhao Wipf Group Page 9 of 17 2/23/2013
10 Tandem RCM Routes 1. T. Honda, H. Namiki, K. Kaneda and H. Mizutani, Org. LeE., 2004, 6, T. Honda, H. Namiki, N. Watanabe and H. Mizutani, Tetrahedron LeE., 2004, 45, Yongzhao Wipf Group Page 10 of 17 2/23/2013
11 Relay RCM Strategy 1. T. R. Hoye, C. S. Jeffrey, M. A. Tennakoon, J. Wang, H. Zhao, J. Am. Chem. Soc. 2004, 126, 10210; 2. K. D. Schwartz, J. D. White, Org. LeE. 2011, 13, Yongzhao Wipf Group Page 11 of 17 2/23/2013
12 Synthesis of (- )- Norsecurinine and (+)- Allonorsecurinine 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: Yongzhao Wipf Group Page 12 of 17 2/23/2013
13 Synthesis of (- )- Norsecurinine and (+)- Allonorsecurinine 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: Yongzhao Wipf Group Page 13 of 17 2/23/2013
14 Synthesis of (- )- Flueggine A 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: Yongzhao Wipf Group Page 14 of 17 2/23/2013
15 Synthesis of (+)- Virosaine B 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: Yongzhao Wipf Group Page 15 of 17 2/23/2013
16 Synthesis of (- )- Virosaine A 1. H. Miyatake- Ondozabal, L. M. Bannwart and K. Gademann. Chem. Commun., 2013, 49, 1921 Yongzhao Wipf Group Page 16 of 17 2/23/2013
17 Summary 5.92% overall yield for (-)-Flueggine A 6.68% overall yield for (+)-Virosaine B Starting from commercially available Weinreb amide. Tandem RRCMs strategy and 1,3-dipolar cycloadditions as two key steps. Yongzhao Wipf Group Page 17 of 17 2/23/2013
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