Stereoselective synthesis of eight-membered cyclic ethers by tandem Nicholas reaction/ring-closing metathesis: A short synthesis of (+)-cis-lauthisan

Organic Letters

Volumn 8, Issue 5, 2006, Pages 871-873

  Ortega, Nuria ^a   Martín, Tomás ^b   Martín, Víctor S ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; LAUTHISAN;

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

CATALYSIS; CYCLIZATION; ETHERS, CYCLIC; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33644960847     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052932j     Document Type: Article

References (46)

1. (a) Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897-1909.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-48 and preceding issues.
3. Alvarez, E.; Candenas, M. L.; Pérez, R.; Ravelo, J. L.; Martín, J. D. Chem. Rev. 1995, 95, 1953-1980.
4. (b) Mori, Y. Chem. Eur. J. 1997, 3, 849-852.
5. (c) Hoberg, L. O. Tetrahedron 1998, 54, 12631-12670.
6. (d) Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 44-122.
7. (e) Marmsäter, F. P.; West, F. G. Chem. Eur. J. 2002, 8, 4346-4353.
8. For representative examples, see: (a) Hirama, M. Oishi, T.; Uehara, H.; Inoue, M.; Maruyama, M.; Oguri, H.; Satake, M. Science 2001, 294, 1904-1907.
9. (b) Crimmins, M. T.; She, J. J. Am. Chem. Soc. 2004, 126, 12790-12791.
10. (c) Clark, J. S.; Kimber, M. C.; Robertson, J.; McErlean, C. S. P.; Wilson, C. Angew. Chem., Int. Ed. 2005, 44, 6157-6162.
11. (a) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660.
12. (b) Rhee, H. J.; Beom, H. Y.; Kim, H.-D. Tetrahedron Lett. 2004, 45, 8019-8022.
13. (c) Denmark, S. E.; Yang S.-M. J. Am. Chem. Soc. 2004, 126, 12432-12440.
14. For the synthesis of cyclic ethers by intramolecular Nicholas reactions, see: (a) Mukai, C.; Yamaguchi, S.; Sugimoto, Y.; Miyakoshi, N.; Kasamatsu, E.; Hanaoka, M. J. Org. Chem. 2000, 65, 6761-6765 and references therein.
15. (b) Kira, K.; Tanda, H.; Hamajima, A.; Baba, T.; Takai, S.; Isobe, M. Tetrahedron 2002, 58, 6485-6492 and references therein.
16. (c) Betancort, J. M.; Martín, T.; Palazón, J. M.; Martín, V. S. J. Org. Chem. 2003, 68, 3216-3224.
17. (a) Green, J. R. Synlett 2001, 353-356.
18. (b) Young, D. G. J.; Burlison, J. A.; Peters, U. J. Org. Chem. 2003, 68, 3494-3497.
19. (c) Yang, Z.-Q.; Geng, X.; Solit, D.; Pratilas, C. A.; Rosen, N.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 7881-7889.
20. Díaz, D. D.; Martín, V. S. Tetrahedron Lett. 2000, 41, 9993-9996.
21. (a) Blunt, J. W.; Lake, R. J.; Munro, M. H. G.; Yorke, S. C. Aust. J. Chem. 1981, 34, 2393-2400.
22. (b) Fukazawa, A. Masamune, T. Tetrahedron Lett. 1981, 22, 4081-4084.
23. For a previously reported synthesis of lauthisan, see: (a) Reference 4b.
24. (b) Carling, R. W.; Holmes, A. B. J. Chem. Soc., Chem. Commun. 1986, 565-567.
25. (c) Kotsuki, H.; Ushio, Y.; Kadota, I.; Ochi, M. J. Org. Chem. 1989, 54, 5153-5161.
26. Tsushima, K.; Murai, A. Chem. Lett. 1990, 761-764.
27. (d) Nicolaou, K. C.; McGarry, D. G.; Somers, P. K.; Kim, B. H.; Ogilvie, W. W.; Yiannikouros, G.; Prasad, C. V. C.; Veale, C. A.; Hark, R. R. J. Am. Chem. Soc. 1990, 112, 6263-6276.
28. (e) Paquette, L. A.; Sweeney, T. J. J. Org. Chem. 1990, 55, 1703-1704.
29. (f) Udding, J. U.; Giesselink, J. P. M.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1994, 59, 6671-6682.
30. (g) Kim, H.; Ziani-Cherif, C.; Oh, J.; Cha, J. K. J. Org. Chem. 1995, 60, 792-793.
31. (h) Suh, Y.-G.; Koo, B.-A.; Kim, E.-N.; Choi, N.-S. Tetrahedron Lett. 1995, 36, 2089-2092.
32. (i) Coster, M. J.; De Voss, J. J. Org. Lett. 2002, 4, 3047-3050.
33. (j) Carreño, M. C.; Des Mazery, R.; Urbano, A.; Colobert, F.; Solladie, G. Org. Lett. 2005, 7, 2039-2042.
34. Martín, V. S.; Woodard, S. S.; Katsuki, T.; Yamada, Y.; Ikeda, M.; Sharpless, K. B. J. Am. Chem. Soc. 1981, 103, 6237-6240.
35. Yadav, J. S.; Shekharam, T.; Gadgil, V. R. J. Chem. Soc., Chem. Commun., 1990, 843.
36. See the Supporting Information for experimental details.
37. (a) Melikyan, G. G.; Bright, S.; Monroe, T.; Hardcastle, K. I.; Ciurash, J. Angew. Chem., Int. Ed. 1998, 37, 163-164.
38. (b) Young, D. G. J.; Burlison, J. A.; Peters, U. J. Org. Chem. 2003, 68, 3494-3497.
39. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382.
40. (a) Chatterjee, A. K.; Grubbs, R. H. Org. Lett. 1999, 1, 1751-1753.
41. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
42. 6-cycloalkyne ethers, see: (a) Liu, T.-Z.; Li, J.-M.; Isobe, M. Tetrahedron 2000, 56, 10209-10219.
43. (b) Reference 5c.
44. Crisóstomo, F. R. P.; Carrillo, R.; Martín, T.; Martín, V. S. Tetrahedron Lett. 2005, 46, 2829-2832.
45. (a) Hosokawa, S.; Isobe, M. Tetrahedron Lett. 1998, 39, 2609-2612.
46. (b) Shibuya, S.; Isobe, M. Tetrahedron 1998, 54, 6677-6698.