Total Synthesis of (- )- Flueggine A And (+)- Virosaine B

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Total Synthesis of (- )- Flueggine A And (+)- Virosaine B Yongzhao Yan Current lit. 2013.2.23 Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: 620 624. Yongzhao Yan @ Wipf Group Page 1 of 17 2/23/2013

(- )- 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/9925831.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, 3888. 3. 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, 3096. Yongzhao Yan @ Wipf Group Page 2 of 17 2/23/2013

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, 3888. 2. 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, 3096. Yongzhao Yan @ Wipf Group Page 3 of 17 2/23/2013

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, 3888. 2. 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, 3096. Yongzhao Yan @ Wipf Group Page 4 of 17 2/23/2013

Synthesis of Securinega Alkaloids 1. S. M. Weinreb, Nat. Prod. Rep., 2009, 26, 758 2. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: 620 624. 3. H. Miyatake- Ondozabal, L. M. Bannwart and K. Gademann. Chem. Commun., 2013, 49, 1921 Yongzhao Yan @ Wipf Group Page 5 of 17 2/23/2013

Diels- Alder Routes 1. P. A. Jacobi, C. A. Blum, R. W. DeSimone and U. E. S. Udong, Tetrahedron LeE., 1989, 30, 7173 7176 2. P. A. Jacobi, C. A. Blum, R. W. DeSimone and U. E. S. Udong, J. Org. Chem., 1991, 113, 5384 5392 3. T. Honda, H. Namiki, M. Kudoh, N. Watanabe, H. Nagase and H. Mizutani, Tetrahedron LeE., 2000, 41, 5927 5930 4. T. Honda, H. Namiki, M. Kudoh, H. Nagase and H. Mizutani,Heterocycles, 2003, 59, 169 187 Yongzhao Yan @ Wipf Group Page 6 of 17 2/23/2013

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, 237 240 2. G. Han, M. G. LaPorte, J. J. Folmer, K. M. Werner and S. M. Weinreb, J. Org. Chem., 2000, 65, 6293 6306 Yongzhao Yan @ Wipf Group Page 7 of 17 2/23/2013

Vinylogous Mannich ReacGon Route 1. S. Liras, J. E. Davoren and J. Bordner, Org. LeE., 2001, 3, 703 706 2. R. Alibes, P. Bayon, P. De March, M. Figueredo, J. Font, E. Garcia- Garcia and D. Gonzalez- Galvez, Org. LeE., 2005, 7, 5107 5109 3. B. M. Trost, R. C. Bunt, R. C. Lemoine and T. L. Calkins, J. Am. Chem. Soc., 2000, 122, 5968 5976 Yongzhao Yan @ Wipf Group Page 8 of 17 2/23/2013

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, 7657 7662 2. H. Miyatake- Ondozabal, L. M. Bannwart and K. Gademann. Chem. Commun., 2013, 49, 1921 Yongzhao Yan @ Wipf Group Page 9 of 17 2/23/2013

Tandem RCM Routes 1. T. Honda, H. Namiki, K. Kaneda and H. Mizutani, Org. LeE., 2004, 6, 87 89 2. T. Honda, H. Namiki, N. Watanabe and H. Mizutani, Tetrahedron LeE., 2004, 45, 5211 5213 Yongzhao Yan @ Wipf Group Page 10 of 17 2/23/2013

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, 248.. Yongzhao Yan @ Wipf Group Page 11 of 17 2/23/2013

Synthesis of (- )- Norsecurinine and (+)- Allonorsecurinine 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: 620 624. Yongzhao Yan @ Wipf Group Page 12 of 17 2/23/2013

Synthesis of (- )- Norsecurinine and (+)- Allonorsecurinine 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: 620 624. Yongzhao Yan @ Wipf Group Page 13 of 17 2/23/2013

Synthesis of (- )- Flueggine A 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: 620 624. Yongzhao Yan @ Wipf Group Page 14 of 17 2/23/2013

Synthesis of (+)- Virosaine B 1. Wei, H., Qiao, C., Liu, G., Yang, Z. and Li, C.- c. Angew. Chem. Int. Ed., 2013, 52: 620 624. Yongzhao Yan @ Wipf Group Page 15 of 17 2/23/2013

Synthesis of (- )- Virosaine A 1. H. Miyatake- Ondozabal, L. M. Bannwart and K. Gademann. Chem. Commun., 2013, 49, 1921 Yongzhao Yan @ Wipf Group Page 16 of 17 2/23/2013

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 Yan @ Wipf Group Page 17 of 17 2/23/2013

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