Enantioselective synthesis of (1R,2S,4S)-7-oxabicyclo[2.2.1]heptan-2-exo-carboxylic acid

Tetrahedron Asymmetry

Volumn 21, Issue 2, 2010, Pages 159-161

  Wirz, Beat ^a   Spurr, Paul ^a   Pfleger, Christophe ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

( 1,2,4 ) 7 OXABICYCLO[ 2.2.1 ]HEPTAN 2 EXO CARBOXYLIC ACID; ACID LIPASE; ADENOSINE A2A RECEPTOR ANTAGONIST; BUTYL ESTER; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; ASYMMETRIC SYNTHESIS; CANDIDA ANTARCTICA; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ENZYME ACTIVITY; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL;

EID: 77949541857     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.12.030     Document Type: Article

References (13)

1. Flohr, A.; Jakob-Roetne, R.; Norcross, R.; Riemer, C. US2004235915.
2. Nelson W., and Allen D. J. Heterocycl. Chem. 9 (1972) 561-568
3. Sundermann B., and Scharf H. Synlett (1996) 703-704
4. Garrigues B., and Oussaid A. J. Organomet. Chem. 585 (1999) 253-255
5. Fraile J., Garcia J., Gomez M., de la Hoz A., Mayoral J., Moreno A., Prieto P., Salvatella L., and Garcia E. Eur. J. Org. Chem. (2001) 2891-2899
6. Rumi L., Pfleger C., Spurr P., Klinkhammer U., and Bannwarth W. Org. Process Res. Dev. 13 (2009) 747-750
7. Spurr, P.; Wirz, B. Patent Application US2008154043.
8. Schueller C.M., Manning D.D., and Kiessling L.L. Tetrahedron Lett. 37 (1996) 8853-8856
9. Abrecht, S.; Karpf, M.; Trussardi, R.; Wirz, B. European Patent EP 1 127 872 B1, 2001.
10. Abrecht S., Cordon Federspiel M., Estermann H., Fischer R., Karpf M., Mair H.-J., Oberhauser T., Rimmler G., Trussardi R., and Zutter U. Chimia 61 (2007) 93-99
11. Personal communication Steven Paul Hanlon and Hans Iding, Hoffmann-La Roche Ltd.
12. Chen C.-S., Fujimoto Y., Girdaukas G., and Sih C.J. J. Am. Chem. Soc. 104 (1982) 7294-7299
13. 3, 400 MHz): δ (ppm) 10.6 (s br, 1H, COOH), 4.86 (d, J = 5.1 Hz, 1H, H-1), 4.69 (t, J = 5.0 Hz, 1H, H-4), 2.67 (dd, J = 9.1, 4.6 Hz, 1H, H-2), 2.06-2.22 (m, 1H, H-3′), 1.69-1.85 (m, 3H, H-3″, H-5′, H-6′), 1.43-1.60 (m, 2H, H-5″, H-6″).