Endo-6-(Hydroxymethyl)bicyclo[3.1.0]hept-3-en-2-one esters and the photochemical challenge: [2+2] cycloaddition versus skeletal rearrangement

Tetrahedron Asymmetry

Volumn 21, Issue 11-12, 2010, Pages 1480-1485

  Liepvre, Matthieu Le ^a   Ollivier, Jean ^a   Aitken, David J ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

[No Author keywords available]

Indexed keywords

(7 OXOBICYCLO[2.2.1]HEPT 5 EN 2 YL)METHYL 3 BUTENOATE; (7 OXOBICYCLO[2.2.1]HEPT 5 EN 2 YL)METHYL 4 PENTENOATE; (7 OXOBICYCLO[2.2.1]HEPT 5 EN 2 YL)METHYLACETATE; 4 HYDROXY 6 (HYDROXYMETHYL)BICYCLO[3.1.0]HEPT 2 ONE; [2 OXOBICYCLO[3.2.0]HEPT 3 EN 6 YL]METHYL 3 BUTENOATE; [2 OXOBICYCLO[3.2.0]HEPT 3 EN 6 YL]METHYL 4 PENTENOATE; [2 OXOBICYCLO[3.2.0]HEPT 3 EN 6 YL]METHYLACETATE; [2 OXOBICYCLO[3.2.0]HEPT 3 EN 6 YL]METHYLPIVALOATE; ACETIC ACID DERIVATIVE; ALKENE; BICYCLO[3.1.0]HEPTENONE DERIVATIVE; ENDO 6 (HYDROXYMETHYL)BICYCLO[3.1.0]HEPT 3 EN 2 ONE ESTER DERIVATIVE; ESTER DERIVATIVE; HEXAHYDRO 1 OXACYCLOBUTA[CD]PENTALEN 4(2H) ONE; NORBORNENONE DERIVATIVE; TRICYCLO[5.2.0.02,5]NONAN 6 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOMER; ISOMER; PHOTOCHEMISTRY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 77956648185     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.05.043     Document Type: Article

References (32)

1. M. Miesch Curr. Org. Synth. 3 2006 327 340
2. K. Ohashi , M. Kawai , N. Ninomiya , C. Taylor , and Y. Kurebayashi Pharmacology 81 2008 144 150
3. Fish, P. V.; Rykmans, T.; Stobie, A.; Wakenhut, F. World Patent 064332, 2006; Chem. Abstr. 2006, 606101.
4. Gladwell, I. R.; Pettman, A. J. World Patent 031115, 2004; Chem. Abstr. 2004, 308394.
5. Derrick A. M. World Patent 031124, 2004; Chem. Abstr. 2004, 308400.
6. Recent examples: R. Tello-Aburto , M.Y. Rios , D.C. Swenson , and H.F. Olivo Tetrahedron Lett. 49 2008 6853 6855
7. I. Shinohara , and H. Nagaoka Tetrahedron Lett. 45 2004 1495 1498
8. F. Peri , E. Binassi , A. Manetto , E. Marotta , A. Mazzanti , P. Righi , N. Scardovi , and G. Rosini J. Org. Chem. 69 2004 1353 1356
9. D. Depré , L.-Y. Chen , and L. Ghosez Tetrahedron 59 2003 6797 6812
10. M. Harmata , and P. Rashatasakhon Tetrahedron Lett. 42 2001 5593 5595
11. Recent examples: N. El-hachach , R. Gerke , M. Noltemeyer , and L. Fitjer Tetrahedron 65 2009 1040 1047
12. S.G. Sethofer , S.T. Staben , O.Y. Hung , and F.D. Toste Org. Lett. 10 2008 4315 4318
13. K. Takasu , S. Nagao , and M. Ihara Tetrahedron Lett. 46 2005 1005 1008
14. Y. Shimada , M. Nakamura , T. Suzuka , J. Matsui , R. Tatsumi , K. Tsutsumi , T. Morimoto , H. Kurosawa , and K. Kakiuchi Tetrahedron Lett. 44 2003 1401 1403
15. M.E. Jung , and P. Davidov Org. Lett. 3 2001 3025 3027
16. P.C.-K. Lo , and M.L. Snapper Org. Lett. 3 2001 2819 2821
17. Illustrative examples: L.A. Paquette , and J.D. Pettigrew Synthesis 2009 379 384
18. V. Mascitti , and E.J. Corey J. Am. Chem. Soc. 128 2006 3118 3119
19. D.F. Taber , and K.J. Frankowski J. Org. Chem. 70 2005 6417 6421
20. M.T. Crimmins , Z. Wang , and L.A. McKerlie J. Am. Chem. Soc. 120 1998 1747 1756
21. M. Miesch , A. Cotté , and M. Franck-Neumann Tetrahedron Lett. 35 1994 7031 7032
22. M. Tanaka , K. Tomioka , and K. Koga Tetrahedron 50 1994 12829 12842
23. K. Yano , M. Isobe , and K. Yoshida J. Am. Chem. Soc. 100 1978 6166 6170
24. K. Yano J. Org. Chem. 42 1977 1728 1733
25. K. Yano Tetrahedron Lett. 1974 1861 1862
26. R.L. Cargill , T.Y. King , A.B. Sears , and M.R. Willcott J. Org. Chem. 36 1971 1423 1428
27. A.P. Marchand Chem. Rev. 89 1989 1011 1033
28. M. Le Liepvre , J. Ollivier , and D.J. Aitken Eur. J. Org. Chem. 2009 5953 5962
29. R.L. Cargill , A.B. Sears , J. Boehm , and M.R. Willcott J. Am. Chem. Soc. 95 1973 4346 4355
30. R.L. Cargill , B.M. Gimarc , D.M. Pond , T.Y. King , A.B. Sears , and M.R. Willcott J. Am. Chem. Soc. 92 1970 3809 3810
31. J.L. Gras , H. Pellissier , and R. Nouguier J. Org. Chem. 54 1989 5675 5677
32. P. Gariboldi , G. Jommi , and M. Sisti Gazz. Chim. Ital. 116 1986 291 301