Probing a biomimetic approach to mycaperoxide B: Hydroperoxidation studies

Synlett

Volumn , Issue 4, 2010, Pages 509-513

  Silva, Eduarda M P ^a   Pye, Richard J ^a   Cardin, Christine ^a   Harwood, Laurence M ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

Cobalt catalyst; Hydroperoxidation; Marine endoperoxide; Michael addition; Mycaperoxide

Indexed keywords

HYDROPEROXIDE; MYCAPEROXIDE B; PEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; HYDROGENATION; PEROXIDATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77955397974     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/S-0029-1219152     Document Type: Article

References (30)

1. Tanaka, J.; Higa, T.; Suwanborirux, K.; Kokpol, U.; Bernardinelli, G.; Jefford, C. W. J. Org. Chem. 1993, 58, 2999.
2. Ovenden, S. P. B.; Capon, R. J. J. Nat. Prod. 1999, 62, 214.
3. Capon, R. J. Eur. J. Org. Chem. 2001, 633.
4. (a) Harwood, L. M.; Robertson, J.; Swallow, S. Synlett 1999, 1359.
5. (b) Harwood, L. M.; Robertson, J.; Swallow, S. Synlett 1999, 185.
6. (a) Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 573.
7. (b) Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 1305.
8. Kato, K.; Yamada, T.; Takai, T.; Inoki, S.; Isayama, S. Bull. Chem. Soc. Jpn. 1990, 63, 179.
9. (a) Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J.; Kim, H.-S.; Wataya, Y. Tetrahedron 2001, 57, 5979.
10. (b) Tokuyasu, T.; Kunikawa, S.; Abe, M.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Begum, K.; Wataya, Y. J. Org. Chem. 2003, 68, 7361.
11. (c) Wu, J.-M.; Kunikawa, S.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; Kim, H.-S.; Wataya, Y. Tetrahedron 2005, 61, 9961.
12. (d) Oh, C. H.; Kim, H. J.; Wu, S. H.; Won, H. S. Tetrahedron Lett. 1999, 40, 8391.
13. Mori, K.; Sugai, T.; Maeda, Y.; Okazaki, T.; Noguchi, T.; Naito, H. Tetrahedron 1985, 41, 5307.
14. Ito, T.; Tokuyasu, T.; Masuyama, A.; Nojima, M.; McCullough, K. J. Tetrahedron 2003, 59, 525.
15. Falck, J. R.; Lai, J.-Y.; Cho, S.-D.; Yu, J. Tetrahedron Lett. 1999, 40, 2903.
16. (a) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
17. (b) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Tetrahedron Lett. 1991, 32, 1175.
18. (c) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Bull. Soc. Chim. Fr. 1993, 130, 336.
19. (d) Baudin, J. B.; Hareau, G.; Julia, S. A.; Lorne, R.; Ruel, O. Bull. Soc. Chim. Fr. 1993, 130, 856.
20. Gesson, J. P.; Jacquesy, J. C.; Renoux, B. Tetrahedron 1989, 45, 5853.
21. +: 470.3791; found: 470.3800.
22. Xu, X.-X.; Dong, H.-Q. Tetrahedron Lett. 1994, 35, 9429.
23. (a) Dussault, P.; Sahli, A.; Westermeyer, T. J. Org. Chem. 1993, 58, 5469.
24. (b) Clark, G. R.; Nikaido, M. M.; Fair, C. K.; Lin, J. J. Org. Chem. 1985, 50, 1994.
25. (c) Schmid, G.; Hofheinz, W. J. Am. Chem. Soc. 1983, 105, 624.
26. Green, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis; Wiley-Interscience: New York, 1981, 188.
27. Tanemura, K.; Suzuki, T.; Horaguchi, T. J. Chem. Soc., Chem. Commun. 1992, 979.
28. Sabitha, G.; Babu, R. S.; Reddy, E. V.; Yadav, J. S. Chem. Lett. 2000, 1074.
29. +: 377.2662; found: 377.2666.
30. -3, F(000) = 784. 2586. Independent reflections were collected on an Oxford Gemini S Ultra Image Plate System. The structures was solved by direct methods and refined on F2 using SHELXL97. Final R = 0.0487, weighted R = 0.1345. These data can be obtained free of charge from The Cambridge Crystallo-graphic Data Centre via www.ccdc.cam.ac.uk/data-request/cifquoting deposition no. CCDC 750510.