Furan Diels-Alder cycloaddition approach to the highly oxygenated core of scyphostatin

Synlett

Volumn , Issue 14, 2006, Pages 2272-2274

  Stevenson, Neil G ^a   De Savi, Chris ^b   Harrity, Joseph P A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Cycloadditions; Epoxides; Lewis acids; Ring opening; Scyphostatin

Indexed keywords

2 CYCLOHEXENONE; 4,5 BIS(TERT BUTYLDIMETHYLSILANYLOXY) 6 METHYL 6 TRIMETHYLSILANYLOXYCYCLOHEX 2 ENONE; 5,6 BIS(TERT BUTYLDIMETHYLSILANYLOXY) 1 METHYL 7 OXABICYCLO[2.2.1]HEPTAN 2 ONE; BICYCLO COMPOUND; KETENE DERIVATIVE; LEWIS ACID; SCYPHOSTATIN; SPHINGOMYELIN PHOSPHODIESTERASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; EPOXIDATION; OXYGENATION;

EID: 33748698031     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949617     Document Type: Article

References (27)

1. Hudlicky, T.; Entwistle, D. A.; Pitzer, K. K.; Thorpe, A. J. Chem. Rev. 1996, 96, 1195.
2. (a) Liu, A.; Liu, Z. Z.; Zou, Z. M.; Chen, S. Z.; Xu, L. Z.; Yang, S. L. Tetrahedron 2004, 60, 3689.
3. (b) Yu, D. Q. Pure Appl. Chem. 1999, 71, 1119.
4. Takahashi, S.; Hishinuma, N.; Koshino, H.; Nakata, T. J. Org. Chem. 2005, 70, 10162.
5. Tanaka, M.; Nara, F.; Suzuki-Konagai, K.; Hosoya, T.; Ogita, T. J. Am. Chem. Soc. 1997, 119, 7871.
6. Schmidt, R. R.; Beitzke, C.; Forrest, A. K. J. Chem. Soc., Chem. Commun. 1982, 909.
7. Kotsuki, H.; Nishizawa, H. Heterocycles 1981, 16, 1287.
8. Brown, D. S.; Paquette, L. A. J. Org. Chem. 1992, 57, 4512.
9. Black, K. A.; Vogel, P. Helv. Chim. Acta 1984, 67, 1612.
10. Kernen, P.; Vogel, P. Helv. Chim. Acta 1993, 76, 2338.
11. Brion, F. Tetrahedron Lett. 1982, 23, 5299.
12. (a) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173.
13. (b) Le Drian, C.; Vieira, E.; Vogel, P. Helv. Chim. Acta 1989, 72, 338.
14. (c) Le Drian, C.; Vionnet, J.-P.; Vogel, P. Helv. Chim. Acta 1990, 73, 161.
15. (d) Arjona, O.; De Dios, A.; Plumet, J.; Saez, B. Tetrahedron Lett. 1995, 36, 1319.
16. Le Drian, C.; Vogel, P. Helv. Chim. Acta 1987, 70, 1703.
17. In the context of the epoxidation and dihydroxylation of 6, there is significant literature precedent for reagent addition to the exo-face of oxabicycles. For a recent synthesis of an endo-epoxide by an indirect route and for leading references see: Shoji, M.; Imai, H.; Mukaida, M.; Sakai, K.; Kakeya, H.; Osada, H.; Hayashi, Y. J. Org. Chem. 2005, 70, 79.
18. -]: 481.2602; found: 481.2601.
19. Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031.
20. Inoue, M.; Yokota, W.; Murugesh, M. G.; Izuhara, T.; Katoh, T. Angew. Chem. Int. Ed. 2004, 43, 4207.
21. For recent synthetic approaches to the epoxycyclohexenone motif, see: (a) Runcie, K. A.; Taylor, R. J. K. Org. Lett. 2001, 3, 3237.
22. (b) Fujioka, H.; Kotoku, N.; Sawama, Y.; Nagatomi, Y.; Kita, Y. Tetrahedron Lett. 2002, 43, 4825.
23. (c) Murray, L. M.; O'Brien, P.; Taylor, R. J. K. Org. Lett. 2003, 5, 1943.
24. (d) Kenworthy, M. N.; McAllister, G. D.; Taylor, R. J. K. Tetrahedron Lett. 2004, 45, 6661.
25. (e) Pitsinos, E. N.; Cruz, A. Org. Lett. 2005, 7, 2245.
26. (f) Takagi, R.; Tojo, K.; Iwata, M.; Ohkata, K. Org. Biomol. Chem. 2005, 3, 2031.
27. (g) Katoh, T.; Izuhara, T.; Yokota, W.; Inoue, M.; Watanabe, K.; Nobeyama, A.; Suzuki, T. Tetrahedron Lett. 2006, 62, 1590.