Formal total syntheses of (+)-prelaureatin and (+)-laurallene by diastereoselective brook rearrangement-mediated [3 + 4] annulation

Journal of Organic Chemistry

Volumn 75, Issue 11, 2010, Pages 3941-3943

  Sasaki, Michiko ^a   Oyamada, Kazuhisa ^a   Takeda, Kei ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BROOK REARRANGEMENT; DIASTEREOSELECTIVE; FORMAL SYNTHESIS; TOTAL SYNTHESIS;

ETHERS;

STEREOSELECTIVITY;

ETHER DERIVATIVE; KETONE DERIVATIVE; LAURALLENE; PRELAUREATIN; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKADIENES; ETHERS; HALOGENATION; OXOCINS; STEREOISOMERISM;

EID: 77953006972     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100708n     Document Type: Article

References (40)

1. Fukuzawa, A.; Takasugi, Y.; Murai, A. Tetrahedron Lett. 1991, 32, 5597-5598
2. Ishihara, J.; Shimada, Y.; Kanoh, N.; Takasugi, Y.; Fukuzawa, A.; Murai, A. Tetrahedron 1997, 53, 8371-8382
3. Fukuzawa, A.; Kurosawa, E Tetrahedron Lett. 1979, 20, 2797-2800
4. Irie, T.; Izawa, H.; Kurosawa, E. Tetrahedron 1970, 26, 851-870
5. Irie, T.; Izawa, M.; Kurosawa, E. Tetrahedron Lett. 1968, 9, 2735-2738
6. Irie, T.; Izawa, M.; Kurosawa, E. Tetrahedron Lett. 1968, 9, 2091-2096
7. Crimmins, M. T.; Elie, A. T. J. Am. Chem. Soc. 2000, 122, 5473-5476
8. Fujiwara, K.; Souma, S.; Mishima, H.; Murai, A. Synlett 2002, 1493-1495
9. Ishihara, J.; Shimada, Y.; Kanoh, N.; Takasugi, Y.; Fukuzawa, A.; Murai, A. Tetrahedron 1997, 53, 8371-8382
10. Saitoh, T.; Suzuki, T.; Sugimoto, M.; Hagiwara, H.; Hoshi, T. Tetrahedron Lett. 2003, 44, 3175-3178
11. Fujiwara, K.; Souma, S.; Mishima, H.; Murai, A. Synlett 2002, 1493-1495
12. Fujiwara, K. J. Synth. Org. Chem. Jpn. 2007, 65, 502-510
13. Kim, H.; Lee, H.; Lee, D.; Kim, S.; Kim, D. J. Am. Chem. Soc. 2007, 129, 2269-2274
14. Sugimoto, M.; Suzuki, T.; Hagiwara, H.; Hoshi, T. Tetrahedron Lett. 2007, 48, 1109-1112
15. Ortega, N.; Martín, T.; Martín, V. S. Eur. J. Org. Chem. 2009, 554-563
16. Adsool, V. A.; Pansare, S. V. Org. Biomol. Chem. 2008, 6, 2011-2015
17. Fujiwara, K. In Topics in Heterocyclic Chemistry; Kiyota, H., Ed.; Springer: Berlin Germany, 2006; Vol. 5, pp 97 - 148.
18. Fujiwara, K.; Yoshimoto, S.; Takizawa, A.; Souma, S.; Mishima, H.; Murai, A.; Kawai, H.; Suzuki, T. Tetrahedron Lett. 2005, 46, 6819-6822
19. Baek, S.; Jo, H.; Kim, H.; Kim, H.; Kim, S.; Kim, D. Org. Lett. 2005, 7, 75-77
20. Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660
21. Krüger, J.; Hoffmann, R. W. J. Am. Chem. Soc. 1997, 119, 7499-7504
22. Burton, J. W.; Clark, J. S.; Derrer, S.; Stork, T. C.; Bendall, J. G.; Holmes, A. B. J. Am. Chem. Soc. 1997, 119, 7483-7498
23. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966
24. Tsushima, K.; Murai, A. Tetrahedron Lett. 1992, 33, 4345-4348
25. Sasaki, M.; Hashimoto, A.; Tanaka, K.; Kawahata, M.; Yamaguchi, K.; Takeda, K. Org. Lett. 2008, 10, 1803-1806
26. Sawada, Y.; Sasaki, M.; Takeda, K. Org. Lett. 2004, 6, 2277-2279
27. For the construction of eight-membered carbocycles, see: Takeda, K.; Sawada, Y.; Sumi, K. Org. Lett. 2002, 4, 1031-1033 For the original Brook rearrangement-mediated [3 + 4] annulation protocol for seven-membered carbocycles, see: Takeda, K.; Takeda, M.; Nakajima, A.; Yoshii, E. J. Am. Chem. Soc. 1995, 117, 6400-6401
28. Takeda, K.; Nakajima, A.; Yoshii, E. Synlett 1996, 753-754
29. Takeda, K.; Nakajima, A.; Takeda, M.; Okamoto, Y.; Sato, T.; Yoshii, E.; Koizumi, T.; Shiro, M. J. Am. Chem. Soc. 1998, 120, 4947-4959
30. Takeda, K.; Nakajima, A.; Takeda, M.; Yoshii, E.; Zhang, J.; Boeckman, R. K., Jr. Org. Synth. 1999, 76, 199-213
31. Takeda, K.; Ohtani, Y. Org. Lett. 1999, 1, 677-679
32. Takeda, K.; Nakane, D.; Takeda, M. Org. Lett. 2000, 2, 1903-1905
33. Nakai, Y.; Kawahata, M.; Yamaguchi, K.; Takeda, K. J. Org. Chem. 2007, 70, 1379 - 1387.
34. Beckman, R. K., Jr.; Liu, X. Synthesis 2002, 2138-2142
35. Cossy, J.; Taillier, C.; Bellosta, V. Tetrahedron Lett. 2002, 43, 7263-7266
36. Davis, F. A.; Vishwakarma, L. C.; Billmers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241-3243
37. The stereostructure of 24 was assigned by spectral comparison with structurally related compounds (9) and confirmed by conversion into 8.
38. Calculations were performed with the Spartan06 program. Spartan06 (Ver. 1.0.1 for Mac); Wavefunction, Inc: Irvine, CA.
39. Iwai, T.; Fujihara, T.; Tsuji, Y. Chem. Commun. 2008, 6251-6215
40. The overall yields of the present, our previous, and Crimminss syntheses from 23 and (R)-1-(benzyloxy)pent-4-en-2-ol to 8 are 7.3% (18 steps), 3.2% (22 steps), and 21.3% (13 steps), respectively.