Total synthesis of (+)-isatisine A

Organic Letters

Volumn 13, Issue 3, 2011, Pages 502-505

  Lee, Jihoon ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; INDOLE ALKALOID; ISATIN; ISATISINE A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISATIS; STEREOISOMERISM; SYNTHESIS;

INDOLE ALKALOIDS; ISATIN; ISATIS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79851501903     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102848w     Document Type: Article

References (24)

1. Liu, J.-F.; Jiang, Z.-Y.; Wang, R.-R.; Zheng, Y.-T.; Chen, J.-J.; Zhang, X.-M.; Ma, Y.-B. Org. Lett. 2007, 9, 4127-4129.
2. (a) Karadeolian, A.; Kerr, M. A. Angew. Chem., Int. Ed. 2010, 49, 1133-1135.
3. (b) Karadeolian, A.; Kerr, M. A. J. Org. Chem. 2010, 75, 6830-6841.
4. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
5. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
6. (a) Hoppe, D.; Kramer, T.; Erdbriigger, C. F.; Egert, E. Tetrahedron Lett. 1989, 30, 1233-1236.
7. (b) Brüns, A.; Wibbeling, B.; Fröhlich, R.; Hoppe, D. Synthesis 2006, 3111-3121.
8. (c) Kollmann, S.; Fröhlich, R.; Hoppe, D. Synthesis 2007, 883-892.
9. (d) Becker, J.; Fröhlich, R.; Salorinne, K.; Hoppe, D. Eur. J. Org. Chem. 2007, 3337-3348.
10. For the preparation of syn and anti-ethoxy allyl silane 7, see the Supporting Information.
11. Lowe, J. T.; Youngsaye, W.; Panek, J. S. J. Org. Chem. 2006, 71, 3639-3642.
12. Kim, J. H.; Lee, S.; Kwon, M.-G.; Park, Y. S.; Choi, S.-K.; Kwon, B.-M. Synth. Commun. 2004, 34, 1223-1228.
13. Ager, D. J.; Fleming, I.; Patel, S. K. J. Chem. Soc, Perkin Trans 1 1981, 2520-2526.
14. Corey, E. J.; Posner, G. H. J. Am. Chem,. Soc. 1968, 90, 5616-5617.
15. For the spectroscopic anlysis, see the Supporting Information.
16. (a) Slee, D. H.; Romano, S. J.; Yu, J.; Nguyen, T. N.; John, J. K.; Raheja, N. K.; Axe, F. U.; Jones, T. K.; Ripka, W. C. J. Med. Chem. 2001, 44, 2094-2107.
17. (b) Tron, G. C.; Pagliai, F.; Grosso, E. D.; Genazzani, A. A.; Sorba, G.. J. Med. Chem. 2005, 48, 3260-3268.
18. (a) Skarpos, H.; Vorob'eva, D. V.; Osipov, S. N.; Odinets, I. L.; Breuer, E.; Roschenthaler, G.-V. Org. Biomol. Chem. 2006, 4, 3669-3674.
19. (b) Abid, M.; Teixeira, L.; Torok, B. Org. Lett. 2008, 10, 933-935.
20. (c) Higuchi, K.; Sato, Y.; Tsuchimochi, M.; Sugiura, K.; Hatori, M.; Kawasaki, T. Org. Lett. 2009, 11, 197-199.
21. (a) Wrona, I. E.; Gabarda, A. E.; Evano, G.; Panek, J. S. J. Am. Chem. Soc. 2005, 127, 15026-1502.
22. (b) Qin, H.-L.; Panek, J. S. Org. Lett. 2008, 10, 2477-2479.
23. (a) Niwa, H.; Hida, T.; Yamada, K. Tetrahedron. Lett. 1981, 22, 4239-4240.
24. (b) Su, Q.; Panek, J. S. J. Am. Chem. Soc. 2004, 126, 2425-2430.