Formal synthesis of (±)-methyl rocaglate using an unprecedented acetyl bromide mediated Nazarov reaction

Journal of the American Chemical Society

Volumn 134, Issue 14, 2012, Pages 6140-6142

  Magnus, Philip ^a   Freund, Wesley A ^a   Moorhead, Eric J ^a   Rainey, Trevor ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYL BROMIDE; ANTI-TUMOR AGENTS; CORE STRUCTURE; FORMAL SYNTHESIS; NATURAL PRODUCTS; NAZAROV CYCLIZATION; NAZAROV REACTION;

CHEMISTRY; SYNTHESIS (CHEMICAL);

BROMINE COMPOUNDS;

ANTINEOPLASTIC AGENT; METHYL ROCAGLATE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; NAZAROV REACTION; NONHUMAN;

ACETATES; ANTINEOPLASTIC AGENTS; BENZOFURANS; CHEMISTRY, PHARMACEUTICAL; CROSS-LINKING REAGENTS; CYCLIZATION; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXYGEN; PLANT EXTRACTS; STEREOISOMERISM;

EID: 84859570038     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja300900p     Document Type: Article

References (46)

1. King, M. L.; Chiang, C.-C.; Ling, H.-C.; Fujita, E.; Ochiai, M.; McPhail, A. T. J. Chem. Soc., Chem. Commun. 1982, 1150-1151
2. Ishibashi, F.; Satasook, C.; Isman, M. B.; Towers, G. H. N. Phytochemistry 1993, 32, 307-310
3. Cui, B.; Chai, H.; Santisuk, T.; Reutrakul, V.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Kinghorn, A. D. Tetrahedron 1997, 53, 17625-17632
4. Hiort, J.; Chaidir, J. H.; Bohnenstengel, F. I.; Nugroho, B. W.; Schnieder, C.; Wray, V.; Witte., L.; Hung, P. D.; Keit, L. C.; Proksch, P. J. Nat. Prod. 1999, 62, 1632-1635
5. For a review of compounds from Aglaia species (Meliaceae), see: Proksch, P.; Edrada, R.; Ebel, R.; Bohnenstengel, F. I.; Nugroho, B. W. Curr. Org. Chem. 2001, 5, 923-938
6. Dumontet, V.; Thoison, O.; Omobuwajo, O. R.; Martin, M.-T.; Perromat, G.; Chiaroni, A.; Riche, C.; Païs, M.; Sévenet, T.; Hadi, A. H. A. Tetrahedron 1996, 52, 6931-6942
7. Ohse, T.; Ohba, S.; Yamamoto, T.; Koyano, T.; Umezawa, K. J. Nat. Prod. 1996, 59, 650-652
8. Nugroho, B. W.; Edrada, R. A.; Güssregen, B.; Wray, V.; Witte., L.; Proksch, P. Phytochemistry 1997, 44, 1455-1461
9. Chaidir, J. H.; Nugroho, B. W.; Bohnenstengel, F. I.; Wray, V.; Witte., L.; Hung, P. D.; Keit, L. C.; Sumaryono, W.; Proksch, P.; Proksch, P. Phytochemistry 1999, 52, 837-842
10. Bringmann, G.; Mühlbacher, J.; Messer, K.; Dreyer, M.; Ebel, R.; Nugroho, B. W.; Wray, V.; Proksch, P. J. Nat. Prod. 2003, 66, 80-85
11. Hwang, B. Y.; Su, B.-N.; Chai, H.; Mi, Q.; Kardono, L. B. S.; Afriastini, J. J.; Riswan, S.; Santarsiero, B. D.; Mesecar, A. D.; Wild, N. R.; Fairchild, C. R.; Vite, G. D.; Rose, W. C.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Swanson, S. M; Kinghorn, A. D. J. Org. Chem. 2004, 69, 3350-3358
12. Correction: J. Org. Chem. 2004, 69, 6156. The correct taxonomic identity of the plant studied is Aglaia foveolata Pannell, not Aglaia silvestris (M. Roemer).
13. Merrill. Kim, S.; Salim, A. A.; Swanson, S. M.; Kinghorn, A. D. Anti-Cancer Agents Med. Chem. 2006, 6, 319-345
14. For the synthesis of (±)- 2 before it was known to be a natural product, see: Kraus, G. A.; Sy, J. O. J. Org. Chem. 1989, 54, 77-83
15. For synthesis of (-)- 1, and the C1-OTMS derivative of 2, see: Trost, B. M.; Greenspan, P. D.; Yang, B. V.; Saulnier, M. G. J. Am. Chem. Soc. 1990, 112, 9022-9024
16. For synthesis of (±)- 2, see: Davey, A. E.; Schaeffer, M. J.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1992, 2657-2666
17. For synthesis of (±)- 1, see: Dobler., M. R.; Bruce, I.; Cederbaum, F.; Cooke, N. G.; Diorazio, L. J.; Hall, R. G.; Irving, E. Tetrahedron Lett. 2001, 42, 8281-8284
18. For synthesis of (±)- 1 and 2 via a putative biomimetic route, see: Gerard, B.; Jones, G., II; Porco, J. A., Jr. J. Am. Chem. Soc. 2004, 126, 13620-13621
19. For synthesis of (±)-rocaglaol, see: Thede, K.; Diedrichs, N.; Ragot, J. P. Org. Lett. 2004, 6, 4595-4597
20. Ragot, J. P.; Thede, K. Eur. J. Org. Chem. 2005, 1731-1735
21. Gerard, B.; Sangji, S.; O'Leary, D. J.; Porco, J. A., Jr. J. Am. Chem, Soc. 2006, 128, 7754-7755
22. For synthesis of (-)- 3, see: Gerard, B.; Cencic, R.; Pelletier, J.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2007, 46, 7831-7834
23. Synthesis of (-)- 3 and (-)- 4, see: El Sous, M.; Khoo, M. L.; Holloway, G.; Owen, D.; Scammells, P. J.; Rizzacasa, M. A. Angew. Chem., Int. Ed. 2007, 46, 7835-7838
24. Magnus, P.; Stent, M. A. H. Org. Lett. 2005, 7, 3853-3855
25. Malona, J. A.; Cariou, K.; Frontier, A. J. J. Am. Chem. Soc. 2009, 131, 7560-7561
26. For recent reviews of the numerous reaction conditions that have been used for Nazarov cyclizations, see: Frontier, A. J.; Collison, C. Tetrahedron 2005, 61, 7577-7606
27. Tius, M. A. Eur. J. Org. Chem. 2005, 2193-2206
28. Denmark, S. E. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: 1991;, Vol. 5, pp 751-781.
29. 1-Oxo Nazarov: Tius, M. A.; Astrab, D. P.; Fang, A. H.; Ousset, J. B.; Trehan, S. J. Am. Chem. Soc. 1986, 108, 3438
30. Santelli-Rouvier, C.; Santelli, M. Synthesis 1983, 429-442
31. Sorensen, T. S.; Rauk, A. Pericyclic reactions; Marchand, A. P.; Lehr, R. E., Eds.; Academic Press: 1977;, Vol. II, pp 1-71.
32. Millar, A. K.; Banghart, M. R.; Beaudry, C. M.; Suh, J. M.; Trauner, D. Tetrahedron 2003, 59, 8919-8930
33. He, W.; Sun, X.; Frontier, A. J. J. Am. Chem. Soc. 2003, 125, 14278-14279
34. Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544-9545
35. Liang, G.; Xu, Y.; Seiple, I. B.; Trauner, D. J. Am. Chem. Soc. 2006, 128, 11022-11023
36. For recent examples of the so-called interrupted Nazarov reaction, see: Dhoro, F.; Tius, M. A. J. Am. Chem. Soc. 2005, 127, 12472-12473
37. Grant, T. N.; West, F. G. Org. Lett. 2007, 9, 3789-3792
38. White, T. D.; West, F. G. Tetrahedron Lett. 2005, 46, 5629-5632
39. Tamao, K.; Kiso, Y.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9268-9269
40. Kondo, Y.; Shiga, F.; Murata, N.; Sakamoto, T.; Yamanaka, H. Tetrahedron 1994, 50, 11803-11812
41. Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297-299
42. Bokhari, S. A. N. N.; Whalley, W. B. J. Chem. Soc. 1963, 5322-5324
43. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183-2186
44. Juenge, E. C.; Beal, D. A. Tetrahedron Lett. 1968, 11, 5819-5820
45. Isaacs, N. Physical Organic Chemistry, 2 nd ed.; Longman Scientific and Technical: U.K., 1995.
46. Briody, J. M.; Satchell, D. P. N. J. Chem. Soc. 1964, 3724-3731