Total synthesis of the marine alkaloid mansouramycin D

Organic Letters

Volumn 16, Issue 1, 2014, Pages 244-246

  Prakash, K S ^a   Nagarajan, Rajagopal ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 (1H INDOL 3 YL) 7 METHYLAMINOISOQUINOLINE 5,8 DIONE; 3-(1H-INDOL-3-YL)-7-METHYLAMINOISOQUINOLINE-5,8-DIONE; ALKALOID; ISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STREPTOMYCES; SYNTHESIS;

ALKALOIDS; ISOQUINOLINES; MOLECULAR STRUCTURE; STREPTOMYCES;

EID: 84891810720     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4032396     Document Type: Article

References (34)

1. Hawas, U. W.; Shaaban, M.; Shaaban, K. A.; Speitling, M.; Maier, A.; Kelter, G.; Fiebig, H. H.; Meiners, M.; Helmke, E.; Laatsch, H. J. Nat. Prod. 2009, 72, 2120
2. Delgado, V.; Ibacache, A.; Theoduloz, C.; Valderrama, J. A. Molecules 2012, 17, 7042
3. Beerlink, J. Total synthese der Mansouramycine A-E aus Streptomyces sp. und Rhodium katalysierte 1,2-Additionen an cyclische Enone. Ph.D. Thesis, University of Göttingen, Germany, 2009. URL: http://ediss.uni-goettingen. de/handle/11858/00-1735-0000-0006-AD4C-2?locale-attribute=en.
4. Milanowski, D. J.; Gustafson, K. R.; Kelley, J. A.; McMahon, J. B. J. Nat. Prod. 2004, 67, 70
5. Alagille, D.; Baldwina, R. M.; Tamagnana, G. D. Tetrahedron Lett. 2004, 45, 6179
6. Wipf, P.; Joo, B.; Nguyen, T.; Lazo, J. S. Org. Biomol. Chem. 2004, 2, 2173
7. For a review on marine natural products, see: Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2011, 28, 196
8. Kametani, T. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley and Sons: New York, 2007; Vol. 3, pp 1-272.
9. Yu, C.; Zhang, Y.; Zhang, S.; Li, H.; Wang, W. Chem. Commun. 2011, 47, 1036
10. Chrzanowska, M.; Rozwadowska, M. D. Chem. Rev. 2004, 104, 3341
11. Shigehisa, H.; Takayama, J.; Honda, T. Tetrahedron Lett. 2006, 47, 7301
12. Itoh, T.; Miyazaki, M.; Fukuoka, H.; Nagata, K.; Ohsawa, A. Org. Lett. 2006, 8, 1295
13. Li, G. -Y.; Li, B. -G.; Yang, T.; Liu, G. -Y.; Zhang, G.-L. Org. Lett. 2006, 8, 3613
14. Honda, T.; Shigehisa, H. Org. Lett. 2006, 8, 657
15. Padwa, A.; Danca, M. D. Org. Lett. 2002, 4, 715
16. Ashley, E. R.; Cruz, E. G.; Stoltz, B. M. J. Am. Chem. Soc. 2003, 125, 15000
17. L. Tietze, F.; Rackelmann, N.; Sekar, G. Angew. Chem., Int. Ed. 2003, 42, 4254
18. Bischler, A.; Napieralski, B. Ber. Dtsch. Chem. Ges. 1893, 26, 1903
19. Gensler, W. J. Organic Reactions; Adams, R., Ed.; Wiley: New York, 2011; Vol. 6, pp 191-206.
20. Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797
21. Zheng, D.; Li, S.; Wu, J. Org. Lett. 2012, 14, 2655
22. Yang, Y.-Y.; Shou, W.-G.; Chen, Z.-B.; Hong, D.; Wang, Y.-G. J. Org. Chem. 2008, 73, 3928
23. Hui, B. W.-Q.; Chiba, S. Org. Lett. 2009, 11, 729 and references therein
24. Huang, Q.; Larock, R. C. J. Org. Chem. 2002, 68, 980
25. Roesch, K. R.; Larock, R. C. J. Org. Chem. 1998, 63, 5306
26. Yu, X.; Wu, J. J. Comb. Chem. 2009, 11, 895
27. Huang, Q.; Hunter, J. A.; Larock, R. C. Org. Lett. 2001, 3, 2973
28. Yang, D.; Burugupalli, S.; Daniel, D.; Chen, Y. J. Org. Chem. 2012, 77, 4466
29. Alfonsi, M.; Dell'Acqua, M.; Facoetti, D.; Arcadi, A.; Abbiati, G.; Rossi, E. Eur. J. Org. Chem. 2009, 2852
30. Huang, Q.; Hunter, J. A.; Larock, R. C. J. Org. Chem. 2002, 67, 3437
31. Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86
32. Little, A.; Porco, J. A., Jr. Org. Lett. 2012, 14, 2862
33. Unsworth, W. P.; Cuthbertson, J. D.; Taylor, R. J. K. Org. Lett. 2013, 15, 3306
34. Trost, B. M.; Dyker, G.; Kulawiec, R. J. J. Am. Chem. Soc. 1990, 12, 7809