Convergent formal synthesis of (±)-roseophilin

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 704-706

  Song, Chuanjun ^a   Liu, Hui ^a   Hong, Meiling ^a   Liu, Yuanyuan ^a   Jia, Feifei ^a   Sun, Li ^a   Pan, Zhenliang ^a   Chang, Junbiao ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CONVERGENT SYNTHESIS; CYCLIZATION REACTIONS; FORMAL SYNTHESIS; ROSEOPHILIN; SHORTEST ROUTE;

NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

MACROCYCLIC COMPOUND; ORGANIC COMPOUND; ROSEOPHILIN; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CONVERGENT FORMAL SYNTHESIS; CYCLIZATION; ORGANIC CHEMISTRY; RACEMIC MIXTURE; REACTION ANALYSIS;

CATALYSIS; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR STRUCTURE; PYRROLES; STEREOISOMERISM;

EID: 84862908375     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201949x     Document Type: Article

References (33)

1. Hayakawa, Y.; Kawakami, K.; Seto, H. Tetrahedron Lett. 1992, 33, 2701-2704
2. Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817-2825
3. Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601-2604
4. Mochizuki, T.; Itoh, E.; Shibata, N.; Nakatani, S.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1998, 39, 6911-6914
5. Luker, T.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220-221
6. Fürstner, A.; Gastner, T.; Weintritt, H. J. Org. Chem. 1999, 64, 2361-2366
7. Harrington, P. E.; Tius, M. A. Org. Lett. 1999, 1, 649-651
8. Bamford, S. J.; Luker, T.; Speckamp, W. N.; Hiemstra, H. Org. Lett. 2000, 2, 1157-1160
9. Trost, B. M.; Doherty, G. A. J. Am. Chem. Soc. 2000, 122, 3801-3810
10. Robertson, J.; Hatley, R. J. D.; Watkin, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 3389-3396
11. Boger, D. L.; Hong, J. J. Am. Chem. Soc. 2001, 123, 8515-8519
12. Harrington, P. E.; Tius, M. A. J. Am. Chem. Soc. 2001, 123, 8509-8514
13. Salamone, S. G.; Dudley, G. B. Org. Lett. 2005, 7, 4443-4445
14. Occhiato, E. G.; Prandi, C.; Ferrali, A.; Guarna, A. J. Org. Chem. 2005, 70, 4542-4545
15. Song, C.; Knight, D. W.; Whatton, M. A. Org. Lett. 2006, 8, 163-166
16. Bitar, A. Y.; Frontier, A. J. Org. Lett. 2009, 11, 49-52
17. For a review, see: Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582-3603
18. Ranu, B. C.; Jana, R. Eur. J. Org. Chem. 2006, 3767-3770, and references cited therein
19. Starostin, E. K.; Furman, D. B.; Ignatenko, A. V.; Barkova, A. P.; Nikishin, G. I. Russ. Chem. Bull., Int. Ed. 2006, 55, 2016-2019
20. Song, C.; Knight, D. W.; Whatton, M. A. Tetrahedron Lett. 2004, 45, 9573-9576
21. Ketcha, D. M.; Carpenter, K. P.; Atkinson, S. T.; Rajagopalan, H. R. Synth. Commun. 1990, 20, 1647-1655
22. Beshara, C.; Thompson, A. J. Org. Chem. 2005, 70, 10607-10610
23. Malona, J. A.; Colbourne, J. M.; Frontier, A. J. Org. Lett. 2006, 8, 5661-5664
24. Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 2036-2056
25. Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29
26. Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900-1923
27. Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633
28. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370
29. Hoveyda, A. H.; Zhugralin, A. R. Nature 2007, 450, 243-251
30. Graening, T.; Schmalz, H.-G. Angew. Chem., Int. Ed. 2003, 42, 2580-2584
31. Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. J. Am. Chem. Soc. 2003, 125, 5393-5407
32. Seki, M.; Mori, Y.; Hatsuda, M.; Yamada, S. J. Org. Chem. 2002, 67, 5527-5536
33. Williams, D. R.; Meyer, K. G. Org. Lett. 1999, 1, 1303-1305