Toward a total synthesis of amphidinolide X and Y. The tetrahydrofuran- containing fragment C12-C21

Organic Letters

Volumn 9, Issue 6, 2007, Pages 989-992

  Rodríguez Escrich, Carles ^a   Olivella, Anna ^a   Urpí, Fèlix ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE X; AMPHIDINOLIDE Y; BROMIDE; FURAN DERIVATIVE; MACROLIDE; ORGANOSELENIUM DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG; ZINC BROMIDE; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

BROMIDES; CATALYSIS; CYCLIZATION; FURANS; MACROLIDES; MODELS, CHEMICAL; ORGANOSELENIUM COMPOUNDS; STEREOISOMERISM; ZINC COMPOUNDS;

EID: 33947593955     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063035y     Document Type: Article

References (44)

1. (a) 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. (b) Tsuda, M.; Izui, N.; Shimbo, K.; Sato, M.; Fukushi, E.; Kawabata, J.; Katsumata, K.; Horiguchi, T.; Kobayashi, J. J. Org. Chem. 2003, 68, 9109.
3. Reviews: (a) Chakraborty, T. K.; Das, S. Curr. Med. Chem.: Anti-Cancer Agents 2001, 1, 131.
4. (b) Kobayashi, J.; Tsuda, M. Nat. Prod. Rep. 2004, 21, 778.
5. For a review on oxacyclic macrodiolides, see: (c) Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348.
6. (a) Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
7. (b) Fürstner, A.; Kattnig, E.; Lepage, O. J. Am. Chem. Soc. 2006, 128, 9194.
8. Chen, Y.; Jin, J.; Wu, J.; Dai, W.-M. Synlett 2006, 1177.
9. (a) Evans, D. A.; Bilodeau, M. T.; Somers, T. C.; Clardy, J.; Cherry, D.; Kato, Y. J. Org. Chem. 1991, 56, 5750.
10. (b) Mas, G.; González, L.; Vilarrasa, J. Tetrahedron Lett. 2003, 44, 8805.
11. 3, cf. Buchanan, J. G.; Craven, D. A.; Wightman, R. H.; Harnden, M. R. J. Chem. Soc., Perkin Trans. 1 1991, 195).
12. (a) Miyazaki, T.; Han-ya, Y.; Tokuyama, H.; Fukuyama, T. Synlett 2004, 477.
13. (b) For a review: Fukuyama, T.; Tokuyama, H. Aldrichimica Acta 2004, 37, 87.
14. 3, proved to be unnecessary.
15. (Z)-1-Iodo-2-methyl-1-pentene (5a) was prepared from propyne, propylmagnesium chloride, and CuBr, followed by iodination, according to: (a) Hoffmann, R. W.; Schlapbach, A. Liebigs Ann. Chem. 1990, 1243.
16. For the preparation of the zincate and its addition to aldehyde 4, see: (b) Marshall, J. A.; Eidam, P. Org. Lett. 2004, 6, 445 and references therein.
17. 2), followed by iodination. See: Negishi, E.; Horn, D. E. V.; Yoshida, T. J. Am. Chem. Soc. 1985, 107, 6639.
18. For recent reviews, see: (a) Gruttadauria, M.; Meo, P. L.; Noto, R. Targets Heterocycl. Syst. 2001, 5, 31.
19. (b) Silva, F. M.; Jones, J.; Mattos, M. C. S. Curr. Org. Synth. 2005, 2, 393.
20. For relevant papers, see: (c) Lipshutz, B. H.; Gross, T. J. Org. Chem. 1995, 60, 3572 and references therein.
21. (d) Bravo, F.; Kassou, M.; Castillón, S. Tetrahedron Lett. 1999, 40, 1187.
22. (e) Bew, S. P.; Barks, J.; Knight, D. W.; Middleton, R. J. Tetrahedron Lett. 2000, 41, 4447.
23. (f) Senda, Y.; Takayanagi, S.; Sudo, T.; Itoh, H. J. Chem. Soc., Perkin Trans. 1 2001, 270.
24. (g) Kang, S. H.; Kang, S. Y.; Park, C. M.; Kwon, H. Y.; Kim, M. Pure Appl. Chem. 2005, 77, 1269.
25. (h) Alonso, F.; Meléndez, J.; Soler, T.; Yus, M. Tetrahedron 2006, 62, 2264 and references therein.
26. Recent examples: (a) Bravo, F.; Castillón, S. Eur. J. Org. Chem. 2001, 507 (β,γ-di-OH).
27. (b) Gruttadaria, M.; Aprile, C.; Riela, S.; Noto, R. Tetrahedron Lett. 2001, 42, 2213 (β,δ-di-OH).
28. (c) Weghe, P. V.; Bourg, S.; Eustache, J. Tetrahedron 2003, 59, 7365 (α,β′-di-OH, Z olefin),
29. (d) Fettes, A.; Carreira, E. M. J. Org. Chem. 2003, 68, 9274 (α,δ′-di-OH) and references therein,
30. (e) Li, D.-R.; Zhang, D.-H.; Sun, C.-Y.; Zhang, J.-W.; Yang, L.; Chen, J.; Liu, B.; Su, C.; Zhou, W.-S.; Lin, G.-Q. Chem. - Eur. J. 2006, 12, 1185 (β,γ-di-OH).
31. (f) Nicolaou, K. C.; Pihko, P. M.; Bernal, F.; Frederick, M. O.; Qian, W.; Uesaka, N.; Diedrichs, N.; Hinrichs, J.; Koftis, T. V.; Loizidou, E.; Petrovic, G.; Rodríquez, M.; Sarlah, D.; Zou, N. J. Am. Chem. Soc. 2006, 128, 2244 (α,γ,δ-tri-OH).
32. Reviews: (a) Tiecco, M. Top. Curr. Chem. 2000, 208, 7.
33. (b) Wirth, T. Angew. Chem., Int. Ed. 2000, 39, 3742.
34. (c) Petragnani, N.; Stefani, H. A.; Valduga, C. J. Tetrahedron 2001, 57, 1411.
35. Also see: (d) Khokhar, S. S.; Wirth, T. Angew. Chem., Int. Ed. 2004, 43, 631 and references therein.
36. Yang, C.-G.; Reich, N. W.; Shi, Z.; He, C. Org. Lett. 2005, 7, 4553.
37. 2 for 1 day, ca. 70% of the same butyrolactone was isolated.
38. Kang, S. H.; Hwang, T. S.; Kim, W. J.; Lim, J. K. Tetrahedron Lett. 1990, 31, 5917. Because stereoselectivities obtained with commercially available PhSeCl were encouraging in the first trials, more sterically hindered reagents such as Lipshutz's 2,4,6-triisopropylphenylselenyl bromide (see refs 11c and 12d) were not investigated.
39. (a) Tiecco, M.; Testaferri, L.; Santi, C. Eur. J. Org. Chem. 1999, 4, 797.
40. (b) Reitz, A. B.; Nortey, S. O.; Maryanoff, B. E.; Liotta, D.; Monahan, R. J. Org. Chem. 1987, 52, 4191.
41. The benzyl (Bn) and p-mefhoxybenzyl (PMB) groups were not convenient as protecting groups because we obtained many byproducts when various cyclizations were attempted with them instead of MEM.
42. Classical review: (a) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.
43. Also see: (b) Parsons, A. Chem. Br. 2002, 38, 42.
44. (c) Perchyonok, V. T. Tetrahedron Lett. 2006, 47, 5163 and references therein.