Total synthesis of amphidinolide X and its 12Z-isomer by formation of the C12-C13 trisubstituted double bond via ring-closing metathesis

Synlett

Volumn , Issue 11, 2008, Pages 1737-1741

  Dai, Wei Min ^a,b   Chen, Yile ^a   Jin, Jian ^a   Wu, Jinlong ^a   Lou, Jianshu ^c   He, Qiaojun ^c  

^a ZHEJIANG UNIVERSITY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

Anti selective aldehyde crotylation; Macrodiolide; Microwave; Ring closing metathesis; Trisubstituted olefin

Indexed keywords

AMPHIDINOLIDE A; CARBON; CARBON 13; RUTHENIUM;

ARTICLE; CELL STRAIN HL 60; CHEMICAL BOND; CHEMICAL REACTION; COMPLEX FORMATION; CYTOTOXICITY; DESILYLATION; HUMAN; HUMAN CELL; IC 50; ISOMER; RING CLOSING METATHESIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 48449090382     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077885     Document Type: Article

References (73)

1. Tsuda, M.; Izui, N.; Shimbo, K.; Sato, M.; Fukushi, E.; Kawabata, J.; Katsumata, K.; Horiguchi, T.; Kobayashi, J. J. Org. Chem. 2003, 68, 5339.
2. (a) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 77.
3. (b) Kobayashi, J.; Kubata, M. J. Nat. Prod. 2007, 70, 451.
4. Tsuda, M; Izui, N.; Shimbo, K.; Sato, M.; Fukushi, E.; Kawabata, J.; Kobayashi, J. J. Org. Chem. 2003, 68, 9109.
5. For the first total syntheses of amphidinolide X and Y, see: (a) Lepage, O.; Kattnig, E.; Furstner, A. J. Am. Chem. Soc. 2004.126, 15970.
6. (b) Fürstner, A.; Kattnig, E.; Lepage, O. J. Am. Chem. Soc. 2006, 128, 9194.
7. For a review, see: Parenty, A.; Moreau, X.; Campagne, J.-M. Chem. Rev. 2006, 106, 911.
8. For reviews, see: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
9. (b) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
10. (c) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
11. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem. Int. Ed. 2003, 42, 4592.
12. (e) Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199.
13. (f) Grubbs, R. H. Tetrahedron 2004, 60,7117.
14. (g) Nicolaou,K. C.; Bulger,P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490.
15. (h) Gradillas, A.; Pérez-Castells, J. Angew. Chem. Int. Ed. 2006, 45, 6086.
16. (i) Schrodi, Y.; Pederson, R. L. Aldrichimica Acta 2007, 40, 45.
17. (j) Hoveyda, A. H.; Zhugralin, A. R. Nature (London) 2007, 450, 243.
18. (k) See also: Handbook of Metathesis, Vol. 1-3; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
19. For the second total synthesis of amphidinolide Y, see: Jin, J.; Chen, Y.; Li, Y.; Wu, J.; Dai, W.-M. Org. Lett. 2007, 9, 2585.
20. For Ru-mediated RCM to macrocyclic trisubstituted E-alkenes, see: (a) Fürstner, A.; Thiel, O. R.; Ackermann, L. Org. Lett. 2001, 3, 449.
21. (b) Nicolaou, K. C.; Vassilikogiannakis, G.; Montagnon, T. Angew. Chem. Int. Ed. 2002, 41, 3276.
22. (c) Nicolaou, K. C.; Montagnon, T.; Vassilikogiannakis, G.; Mathison, C. J. N.J. Am. Chem. Soc. 2005 127, 8872.
23. (d) Ichige, T.; Kamimura, S.; Mayumi, K.; Sakamoto, Y.; Terashita, S.; Ohteki, E.; Kanoh, N.; Nakata, M. Tetrahedron Lett. 2005, 46, 1263.
24. (e) Alexander, M. D.; Fontaine, S. D.; La Clair, J. J.; DiPasquale, A. G.; Rheingold, A. L.; Burkart, M. D. Chem. Commun. 2006, 4602.
25. (f) Trost, B. M.; Dong, G.; Vance, J. A. J. Am. Chem. Soc. 2007, 129, 4540.
26. (g) Feyen, F.; Jantsch, A.; Altmann, K.-H. Synlett 2007, 415.
27. (h) For Ru-mediated RCM to macrocyclic trisubstituted Z-alkenes or E/Z mixtures, see: Vassilikogiannakis, G.; Margaros, I.; Tofi, M. Org. Lett. 2004, 6, 205. (i) Nicolaou, K. C.; Xu, H. Chem. Commun. 2006, 600.
28. (j) Park, P. K.; O'Malley, S. J.; Schmidt, D. R.; Leighton, J. L. J. Am. Chem. Soc. 2006, 128, 2796.
29. (k) Smith, A. B. III; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2006, 128, 5292.
30. (l) Larrosa, I.; Da Silva, M. I.; Gómez, P. M.; Hannen, P.; Ko, E.; Lenger, S. R.; Linke, S. R.; White, A. J. P.; Wilton, D.; Barrett, A. G. M. J. Am. Chem. Soc. 2006, 128, 14042.
31. (m) Alhamadsheh, M. M.; Gupta, S.; Hudson, R. A.; Perera, L.; Tillekeratne, L. M. V. Chem. Eur. J. 2008, 14, 570.
32. (n) For Mo-mediated RCM to macrocyclic trisubstituted Z-alkenes or E/Z mixtures, see: Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302; and references cited therein.
33. (o) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
34. (p) Content, S.; Dutton, C. J.; Roberts, L. Bioorg. Med. Chem. Lett. 2003, 13, 321.
35. (a) Chen, Y.; Jin, J.; Wu, J.; Dai, W.-M. Synlett 2006, 1177.
36. (b) For an alternative synthesis, see: Rodríguez-Escrich, C.; Olivella, A.; Urpí, F.; Vilarrasa, J. Org. Lett. 2007, 9, 989.
37. (a) Brown, H. C.; Bhat, K. J. Am. Chem. Soc. 1986, 108, 293.
38. (b) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 294.
39. (c) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
40. (d) Benowitz, A. B.; Fidanze, S.; Small, P. L. C.; Kishi, Y. J. Am. Chem. Soc. 2001, 123, 5128.
41. Hackman, B. M.; Lombardi, P. J.; Leighton, J. L. Org. Lett. 2004, 6, 4375.
42. Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903.
43. 1H NMR spectrum of the product mixture.
44. (a) Heckrodt, T. J.; Mulzer, J. Synthesis 2002, 1857.
45. (b) Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404.
46. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
47. (a) McMurry, J. E.; Wong, G. B. Synth. Commun. 1972, 2, 389; and references cited therein.
48. (b) For microwave-assisted cleavage of aromatic methyl esters, see: Sheppard, G. S.; Wang, J.; Kawai, M.; Fidanze, S. D.; BaMaung, N. Y.; Erickson, S. A.; Barnes, D. M.; Tedrow, J. S.; Kolaczkowski, L.; Vasudevan, A.; Park, D. C.; Wang, G. T.; Sanders, W. J.; Mantei, R. A.; Palazzo, F.; Tucker-Garcia, L.; Lou, P.; Zhang, Q.; Park, C. H.; Kim, K. H.; Petros, A.; Olejniczak, E.; Nettesheim, D.; Hajduk, P.; Henkin, J.; Lesniewski, R.; Davidsen, S. K.; Bell, R. L. J. Med. Chem. 2006, 49, 3832.
49. (a) Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
50. (b) Nevalainen, M.; Koskinen, A. M. P. Angew. Chem. Int. Ed. 2001, 40, 4060.
51. (a) Jafarpour, L.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 5416.
52. (b) Fürstner, A.; Hill, A. F.; Liebl, M.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601.
53. (c) For use of an analogous indenylidene ruthenium complex of 24 in the synthesis of the ADE-ring system of Nakadomarin A, see: Fürstner, A.; Guth, O.; Düffels, A.; SeideL G.; Liebl, M.; Gabor, B.; Mynott, R. Chem. Eur. J. 2001, 7, 4811.
54. (d) For recent studies on comprehensive comparison of RCM initiators, see: Clavier, H.; Nolan, S. P. Chem Eur. J. 2007, 13, 8029.
55. (e) Bieniek, M.; Michrowska, A.; Usanov, D. L.; Grela, K. Chem. Eur. J. 2008, 14, 806.
56. -2 mmol) were added after 24, 48, and 72 h, respectively. After refluxing for a total of 4 d, the reaction mixture was concentrated to <1 mL on a rotary evaporator
57. 3): δ = 7.12 (dd, J = 15.8, 7.2 Hz, 1 H), 5.79 (dd, J = 15.8, 1.6 Hz, 1 H), 5.20 (m, 2 H), 4.95 (d, J = 10.3 Hz, 1 H), 3.96 (dt, J = 11.2, 3.6 Hz, 1 H), 2.78 (m, 1 H), 2.69 (dd, J = 16.6,6.1 Hz, 1 H), 2.69 (m, 1 H), 2.58 (dd, J = 13.6,3.9 Hz, 1 H), 2.58 (dd, J = 16.5, 7.5 Hz, 1 H), 2.41 (dd, J = 13.3, 6.3 Hz, 1 H), 2.18 (m, 1 H), 2.17 (m, 1 H), 2.14 (s, 3 H), 2.12 (m, 1 H), 1.94 (tt, J = 13.5, 3.3 Hz, 1 H), 1.75 (dd, J = 13.9, 2.4 Hz, 1 H), 1.55 (s, 3 H), 1.54 (m, 1 H), 1.50 (m, 2 H)
58. Remote control of alkene geometry by endocyclic groups in ring-closing metathesis has been reported. For examples of formation of disubstituted macrocyclic alkenes, see: (a) Meng, D.; Su, D.-S.; Balog, A.; Bertinato, P.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. J. Am. Chem. Soc. 1997, 119, 2733.
59. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731.
60. (c) Fürstner, A.; Dierkes, T.; Thiel, O. R.; Blanda, G. Chem. Eur. J. 2001, 7, 5286.
61. (d) Aïssa, C.; Riveiros, R.; Ragot, J.; Fürstner, A. J. Am. Chem. Soc. 2003, 125, 15512.
62. (e) Couladouros, E. A.; Mihou, A. P.; Bouzas, E. A. Org. Lett. 2004, 6, 977.
63. (f) Castoldi, D.; Caggiano, L.; Panigada, L.; Sharon, O.; Costa, A. M.; Gennari, C. Angew. Chem. Int. Ed. 2005, 44, 588.
64. (g) Matsumura, T.; Akiba, M.; Arai, S.; Nakagawa, M.; Nishida, A. Tetrahedron Lett. 2007, 48, 1265.
65. (h) Mohapatra, D. K.; Ramesh, D. K.; Giardello, M. A.; Chorghade, M. S.; Gurjara, M. K.; Grubbs, R. H. Tetrahedron Lett. 2007, 48, 2621.
66. (i) For examples of formation of trisubstituted macrocyclic alkenes, see: Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073.
67. (j) Nicolaou, K. C.; Vassilikogiannakis, G.; Montagnon, T. Angew. Chem. Int. Ed. 2002, 41, 3276.
68. (k) Nicolaou, K. C.; Montagnon, T.; Vassilikogiannakis, G.; Mathison, C. J. N. J. Am. Chem. Soc. 2005, 127, 8872.
69. (l) Vassilikogiannakis, G.; Margaros, I.; Tofi, M. Org. Lett. 2004, 6, 205.
70. (m) Alhamadsheh, M. M.; Gupta, S.; Hudson, R. A.; Perera, L.; Tillekeratne, L. M. V. Chem. Eur. J. 2008, 14, 570.
71. (n) Trost, B. M.; Dong, G.; Vance, J. A. J. Am. Chem. Soc. 2007, 129, 4540.
72. (o) Ramírez-Fernández, J.; Collado, I. G.; Hernández-Galán, R. Synlett 2008, 339;
73. see also ref. 7.