A Convergent Synthesis of the Macrocyclic Core of Cytotrienins: Application of RCM for Macrocyclization

Organic Letters

Volumn 6, Issue 4, 2004, Pages 525-528

  Evano, Gwilherm ^a   Schaus, Jennifer V ^a   Panek, James S ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; COPPER COMPLEX; CYTOTRIENIN DERIVATIVE; LACTAM DERIVATIVE; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

AMIDATION; APOPTOSIS; ARTICLE; CHEMICAL BOND; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; RING CLOSING METATHESIS;

ALKENES; ANILINE COMPOUNDS; APOPTOSIS; CATALYSIS; COPPER; CYCLIZATION; INDICATORS AND REAGENTS; LACTAMS; MOLECULAR STRUCTURE; RIFAMYCINS; STEREOISOMERISM;

EID: 1342311500     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036284k     Document Type: Article

References (34)

1. (a) Sugita, M.; Natori, Y.; Sasaki, T.; Furihata, K.; Shimazu, A.; Seto, H.; Otake, N. J. Antibiot. 1982, 35, 1460-1466.
2. (b) Sugita, M.; Sasaki, T.; Furihata, K.; Shimazu, A.; Seto, H.; Otake, N. J. Antibiot. 1982, 35, 1467-1473.
3. (c) Smith, A. B., III; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J. ; Barbosa, J.; Funayama, S.; Komiyama, K.; Omura, S. J. Am. Chem. Soc. 1996, 118, 8308-8315.
4. (a) Funyama, S.; Okada, K.; Komiyama, K.; Umezawa, I. J. Antibiot. 1985, 38, 1107-1109.
5. (b) Funyama, S.; Okada, K.; Iwasaki, K.; Komiyama, K.; Umezawa, I. J. Antibiot. 1985, 38, 1677-1683.
6. (c) Nomoto, H.; Katsumata, S.; Takahashi, K.; Funayama, S.; Komiyama, K. ; Umezawa, I.; Omura, S. J. Antibiot. 1989, 42, 479-481.
7. (a) Hosokawa, N.; Naganawa, H.; Inuma, H.; Hamada, M.; Takeuchi, T.; Kanbe, T.; Hori, M. J. Antibiot. 1995, 48, 471-478.
8. (b) Smith, A. B., III; Barbosa, J.; Hosokawa, N.; Naganawa, H.; Takeuchi, T. Tetrahedron Lett. 1998, 39, 2891-2894.
9. (a) Zhang, H. P.; Kakeya, H.; Osada, H. Tetrahedron Lett. 1997, 38, 1789-1792.
10. (b) Osada, H.; Kakeya, H.; Zhang, H. P.; Kobinata, K. PCT Int. Appl. WO 9823594, 1998.
11. Kakeya, H.; Zhang, H. P.; Kobinata, K.; Onose, R.; Onozawa, C.; Kudo, T. ; Osada, H. J. Antibiot. 1997, 50, 370-372.
12. Zhang, H. P.; Kayeka, H.; Osada, H. Tetrahedron Lett. 1998, 39, 6947-6948.
13. Smith, A. B., III.; Barbosa, J.; Wong, W.; Wood, J. L. J. Am. Chem. Soc. 1996, 118, 8316-8328.
14. Masse, C. E.; Yang, M.; Solomon, J.; Panek, J. S. J. Am. Chem. Soc. 1998, 120, 4123-4134.
15. Smith, A. B., III; Wan, Z. J. Org. Chem. 2000, 65, 3738-3753.
16. For recent reviews, see: (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
17. For recent reviews, see: (a) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
18. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
19. (a) Abiko, A.; Liu, J. F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586-2587.
20. (b) Inoue, T.; Liu, J. F.; Buske, D. C.; Abiko, A. J. Org. Chem. 2002, 67, 5250-5256.
21. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
22. (a) Levin, J. I.; Turos, E.; Weinreb, S. M. Synth. Commun. 1982, 12, 989-993.
23. (b) Shimizu, T.; Osako, K.; Nakata, T. Tetrahedron Lett. 1997, 38, 2685-2688.
24. (c) Huang, P. Q.; Zheng, X.; Deng, X. M. Tetrahedron Lett. 2001, 42, 9039-9041.
25. Williams, J. M.; Jobson, R. B.; Yasuda, N.; Marchesini, G.; Dolling, U. H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461-5464.
26. Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100.
27. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Organomet. Chem. 1985, 292, 311-318.
28. Keck, G. E.; Romer, D. R. J. Org. Chem. 1993, 58, 6083-6089.
29. nBuLi, THE.
30. (a) For construction of a conjugated, macrocyclic (E,Z,Z)-triene using RCM, see: Wang, X.; Porco, J. A., Jr. J. Am. Chem. Soc. 2003, 125, 6040-6041.
31. (b) For an attempt to construct a conjugated, macrocyclic triene using RCM, see: Wagner, J.; Cabrejas, L. M. M.; Grossmith, C. E.; Papageorgiou, C.; Senia, F.; Wagner, D.; France, J.; Nolan, S. P. J. Org. Chem. 2000, 65, 9255-9260.
32. The (E,E) stereochemistry of the diene 30 was assigned on the basis of the coupling constants.
33. For a precedent of formation of a diene starting from a bis-1,3-diene by RCM, see ref 20a.
34. The (E,E,E) stereochemistry of the triene 5 was assigned on the basis of the coupling constants between the two protons of the newly created olefin.