Total synthesis of (±)-communesin F via a cycloaddition with indol-2-one

Journal of the American Chemical Society

Volumn 134, Issue 41, 2012, Pages 16941-16943

  Belmar, Johannes ^a   Funk, Raymond L ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCTS; RAPID CONSTRUCTION; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

CHEMISTRY;

COMMUNESIN F; INDOL 2 ONE; INDOLE DERIVATIVE; NATURAL PRODUCT; TRYPTOPHOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; STEREOCHEMISTRY; SYNTHESIS;

CYCLIZATION; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84867557708     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja307277w     Document Type: Article

References (29)

1. Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355
2. Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, K.; Proksch, P. J. Nat. Prod. 2004, 67, 78
3. Hayashi, H.; Matsumoto, H.; Akiyama, K. Biosci., Biotechnol., Biochem. 2004, 68, 753
4. Dalsgaard, P. W.; Blunt, J. W.; Munro, M. H. G.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 2005, 68, 258
5. Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124
6. Crawley, S. L.; Funk, R. L. Org. Lett. 2003, 5, 3169
7. May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44, 1203
8. Crawley, S. L.; Funk, R. L. Org. Lett. 2006, 8, 3995
9. May, J. A.; Stoltz, B. Tetrahedron 2006, 62, 5262
10. George, J. H.; Adlington, R. M. Synlett 2008, 2093
11. Boal, B. W.; Schammel, A. W.; Garg, N. K. Org. Lett. 2009, 11, 3458
12. Artman, G. D.; Weinreb, S. M. Org. Lett. 2003, 5, 1523
13. Sabahi, A.; Novikov, A.; Rainier, J. D. Angew. Chem., Int. Ed. 2006, 45, 4317
14. Evans, M. A.; Sacher, J. R.; Weinreb, S. M. Tetrahedron 2009, 65, 6712
15. Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008
16. Yang, J.; Wu, H. X.; Shen, L. Q.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794
17. Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem., Int. Ed. 2010, 49, 2000
18. Zuo, Z. W.; Xie, W. Q.; Ma, D. W. J. Am. Chem. Soc. 2010, 132, 13226
19. Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068
20. Wu, H. X.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132, 14052
21. Fuchs, J. R.; Funk, R. L. Org. Lett. 2005, 7, 677
22. For a seminal investigation of substitution reactions of 3-bromo-3-methylindolin-2-ones with hetero nucleophiles that most likely involved the intermediacy of 3-methylindol-2-one, see: Hinman, R. L.; Bauman, C. P. J. Org. Chem. 1964, 29, 2431
23. For reviews, see: Szostak, M.; Aubé J. Org. Biomol. Chem. 2011, 9, 27 and ref 1 therein
24. Ku, J. M.; Jeong, B. S.; Jew, S. S.; Park, H. G. J. Org. Chem. 2007, 72, 8115
25. Yamamoto, H.; Ho, E.; Namba, K.; Imagawa, H.; Nishizawa, M. Chem.-Eur. J. 2010, 16, 11271
26. Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1985, 26, 5543
27. However, the construction of a pyrimidalized, fused lactam from an amino ester using triisobutylaluminum in the context of a classic cephalosporin C total synthesis serves as useful precedent, see: Woodward, R. B.; Heusler, K.; Fosteli, J.; Naegeli, P.; Oppolzer, W.; Ramage, R.; Ranganathan, S.; Vorbrüggen, H. J. Am. Chem. Soc. 1966, 88, 852
28. Basha, A.; Lipton, M.; Weinreb, S. M. Tetrahedron Lett. 1977, 4171
29. Abel-Magid, A. F.; Mehrman, S. J. Org. Process Res. Dev. 2006, 10, 971