Synthesis of methyl 1-hydroxy-6-oxo-2-cyclohexenecarboxylate, a component of salicortin and tremulacin, and the monomer of idesolide

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 8099-8102

  Richardson, Amie M ^a   Chen, Chun Hsing ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENOL ETHER; SALICORTIN;

DIMERIZATION; HYDROLYSIS; MONOMERS; OXIDATION; SCANNING ELECTRON MICROSCOPY; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

AZIRIDINE DERIVATIVE; CAMPHORSULFONYLOXAZIRIDINE; CARBOXYLIC ACID DERIVATIVE; CYCLOHEXENE DERIVATIVE; HEMOSTATIC AGENT; IDESOLIDE; METHYL 1 HYDROXY 6 OXO 2 CYCLOHEXENECARBOXYLATE; SALICORTIN; SALICYLIC ACID METHYL ESTER; TREMULACIN; UNCLASSIFIED DRUG;

ARTICLE; BIRCH REDUCTION; DIMERIZATION; HYDROLYSIS; OPTICS; OXIDATION; RACEMIC MIXTURE; SCANNING ELECTRON MICROSCOPY; SYNTHESIS;

CARBOXYLIC ACIDS; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXENES; GLUCOSIDES; HYDROLYSIS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 35348921128     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701512w     Document Type: Article

References (32)

1. Kim, S. H.; Sung, S. H.; Choi, S. Y.; Chung, Y. K.; Kim, J.; Kim, Y. C. Org. Lett. 2005, 7, 3275-3277.
2. Ekabo, O. A.; Farnsworth, N. R.; Santisuk. T.; Reutrakul, V. J. Nat. Prod. 1993, 56, 699-707.
3. Rasmussen, B.; Nkurunziza, A.-J.; Witt, M.; Oketch-Rabah, H. A.; Jaroszewski, J. W.; Stærk, D. J. Nat. Prod. 2006, 69, 1300-1304.
4. Kim, S. H.; Jang, Y. P.; Sung, S. H.; Kim, Y. C. Planta Med. 2007, 73, 167-179.
5. Jeffreys, D. Aspirin: The Remarkable Story of a Wonder Drug; Bloomsbury: New York, 2004.
6. Mahdi, J. G.; Mahdi, A. J.; Mahdi, A. J.; Bowen, I. D. Cell Prolif. 2006, 39, 147-155.
7. (a) Pearl, I. A.; Darling, S. F. Tetrahedron Lett. 1970, 11, 3827-3830.
8. (b) Pearl, I. A.; Darling, S. F. Phytochemistry 1971, 10, 3161-3166.
9. Chou, C.-J.; Lin, L.-C.; Tsai, W.-J.; Hsu, S.-Y.; Ho, L.-K. J. Nat. Prod. 1997, 60, 375-377.
10. Ishikawa, T.; Nishigaya, K.; Takami, K.; Uchikoshi, H.; Chen, I.-S.; Tsai, I.-L. J. Nat. Prod. 2004, 67, 659-663.
11. (a) Julkunen-Tiitto, R.; Meier, B. J. Nat. Prod. 1992, 55, 1204-1212.
12. (b) Ruuhola, T.; Julkunen-Tiitto, R.; Vainiotalo, P. J. Chem. Ecol. 2003, 29, 1083-1097.
13. Jauch, J.; Schurig, V.; Walz, L. Z. Kristallogr. 1991, 196, 255-260.
14. Shurvell, H. F.; Petelenz, B. U.; Hester, R. E.; Girling, R. B. J. Mol. Struct. 1982, 84, 11-23.
15. Bernart, M. W.; Gerwick, W. H.; Corcoran, E. E.; Lee, A. Y.; Clardy, J. Phytochemistry 1992, 31, 1273-1276.
16. (a) Duggan, J. C.; Urry, W. H.; Schaefer, J. Tetrahedron Lett. 1971, 4197-4200.
17. (b) Heyns, K.; Köll, P. Chem. Ber. 1971, 104, 3835-3841.
18. (c) Heyns, K.; Köll, P. Chem. Ber. 1973, 106, 611-622.
19. (d) Yates, P.; Langford, G. E. Can. J. Chem. 1981, 59, 344-355.
20. (e) Freimund, S.; Köpper, S. Carbohydr. Res. 1998, 308, 195-200.
21. (f) Andersen, S. M.; Lundt, I.; Marcussen, J.; Yu, S. Carbohydr. Res. 1999, 320, 250-256.
22. (a) Christoffers, J.; Werner, T.; Frey, W.; Baro, A. Eur. J. Org. Chem. 2003, 4879-4886.
23. (b) Baucherei, X.; Levoirier, E.; Uziel, J.; Juge, S. Tetrahedron Lett. 2000, 41, 1385-1387.
24. (c) Christoffers, J. J. Org. Chem. 1999, 64, 7668-7669.
25. Kato, M.; Kamat, V. P.; Yoshikoshi, A. Synthesis 1988, 699-701.
26. Schultz, A. G.; Harrington, R. E.; Holoboski, M. A. J. Org. Chem. 1992, 57, 2973-2976.
27. Nagarathnam, D.; Cushman, M. Tetrahedron 1991, 47, 5071-5076.
28. Lipshutz, B. H.; Pegram, J. J. Tetrahedron Lett. 1980, 21, 3343-3346.
29. Vakalopoulos, A.; Hoffmann, H. M. R. Org. Lett. 2000, 2, 1447-1450.
30. Etter, M. C.; MacDonald, J. C.; Bernstein, J. Acta Crystallogr., Sect. B: Struct. Sci. 1990, 46, 256-262.
31. Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715-3717.
32. Tanyeli, C.; Sezen, B.; Demir, A. S.; Alves, R. B.; Arseniyadis, S. Tetrahedron: Asymmetry 1999, 10, 1129-1133.