Synthesis of two new azabicyclophosphinic acids as constrained analogues of TPMPA

Synlett

Volumn , Issue 19, 2005, Pages 3008-3010

  Orain, David ^a   Mattes, Henri ^a  

^a Novartis Institute for BioMedical Research Basel   (Switzerland)

Author keywords

Bicyclic compounds; Cyclizations; Medicinal chemistry; Phosphorus; Receptors

Indexed keywords

ALKADIENE; PHOSPHINIC ACID DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 28844501346     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921902     Document Type: Article

References (14)

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3. Hanrahan, J. R.; Mewett, K. N.; Chebib, M.; Burden, P. M.; Johnston, G. A. R. J. Chem. Soc., Perkin Trans. 1 2001, 2389.
4. Chebib, M.; Vandenberg, R. J.; Johnston, G. A. R. Br. J. Pharmacol. 1997, 122, 1551.
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6. Quin, L. D.; Middlemas, E.; Rao Nandakumar, S.; Miller, R. W.; McPhail, A. T. J. Am. Chem. Soc. 1982, 104, 1893.
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8. (b) Conway, S. J.; Miller, J. C.; Bond, A. D.; Clark, B. P.; Jane, D. E. J. Chem. Soc., Perkin Trans. 1 2002, 14, 1625.
9. 4 and concentrated in vacuo to afford a crude yellow oil (2 g). Purification was achieved by flash chromatography over silica gel using EtOAc-MeOH (100:0 to 80:20) as eluent. After concentration of the fractions, a yellow paste (1.05 g, 63%) was obtained.
10. 2O): δ = 3.55 (m, 2 H), 3.03 (m, 2 H), 2.85 (m, 2 H), 1.82 (m, 2 H), 1.40 (m, 2 H).
11. (a) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1994, 35, 9537.
12. (b) Trost, B. M.; Chen, S.-F. J. Am. Chem. Soc. 1986, 108, 6053.
13. Protocol for purification over DOWEX resin see: Dumond, Y. R.; Montchamp, J.-L. J. Organomet. Chem. 2002, 653, 252.
14. 2O): δ = 5.87 (d, J = 31.7 Hz, 1 H), 3.79 (d, J = 14.0 Hz, 1 H), 3.56 (d, J = 15.9 Hz, 1 H), 3.42 (dd, J = 12.8 Hz, J = 2.4 Hz, 1 H), 3.01 (m, 1 H), 2.30 (m, 1 H), 2.15 (m, 2 H), 2.00 (m, 1 H), 1.63 (m, 1 H).