Determination of the enantiomeric purity of the phytoalexins spirobrassinins by 1H NMR using chiral solvation

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 22, 2004, Pages 5469-5471

  Pedras, M S C ^a   Hossain, M ^a   Sarwar, M G ^a   Montaut, S ^a  

^a UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

1 Methoxyspirobrassinin; Chiral solvation; Enantiomeric purity; Spirobrassinin

Indexed keywords

1 (9 ANTHRYL) 2,2,2 TRIFLUOROETHANOL; 1 METHOXYSPIROBRASSININ; FLUORINE DERIVATIVE; PHYTOALEXIN; PROTON; SOLVENT; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHIRALITY; CHROMATOGRAPHY; ENANTIOMER; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION;

MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PLANT EXTRACTS; SOLVENTS; SPIRO COMPOUNDS; STEREOISOMERISM; TERPENES; THIAZOLES;

TRIFLUORO;

EID: 5144228818     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.09.014     Document Type: Article

References (19)

1. J.A. Bailey J.W. Mansfield Phytoalexins 1982 Blackie & Son Glasgow, UK 334
2. Reviewed in: M.S.C. Pedras, F.I. Okanga, I.L. Zaharia, and A.Q. Khan Phytochemistry 53 2000 161 176
3. For a recent review, see: M.S.C. Pedras, M. Jha, and P.W.K. Ahiahonu Curr. Org. Chem. 7 2003 1635 1647
4. M. Suchy, P. Kutschy, K. Monde, H. Goto, N. Harada, M. Takasugi, M. Dzurilla, and E. Balentova J. Org. Chem. 66 2001 3940 3947
5. M.S.C. Pedras, S. Montaut, and M. Suchy J. Org. Chem. 69 2004 4471 4476
6. Pedras, M. S. C.; Ahiahonu, P. W. K. J. Chem. Ecol. 2004, in press
7. 3CN, 20:80, 1 mL/min
8. T.J. Wenzel Trends Org. Chem. 8 2000 51 64
9. D. Parker Chem. Rev. 91 1991 1441 1457
10. W.H. Pirkle, and D.J. Hoover Topics Stereochem. 13 1982 263 331
11. P. Kutschy, M. Suchy, K. Monde, N. Harada, R. Maruskova, Z. Curillova, M. Dzurilla, M. Miklosova, R. Mezencev, and J. Mojzis Tetrahedron Lett. 43 2002 9489 9492
12. Pedras, M. S. C.; Sarwar, M. G., unpublished results
13. 2, Ref. 4
14. 3 M. Takasugi, K. Monde, N. Katsui, and A. Shirata Chem. Lett. 22 1987 1631 1632
15. -1
16. 2O exchangeable), 6.81 (dd, J = 7.5, 7.5 Hz, 1H), 6.65 (dd, J = 7.5, 7.5 Hz, 1H), 6.11 (d, J = 7.5 Hz, 1H), 4.62 (d, J = 15 Hz, 1H), 4.18 (d, J = 15 Hz, 1H), 2.16 (s, 3H)
17. 6) δ 6.97 (d, J = 7.5 Hz, 1H), 6.89 (dd, J = 7.5, 7.5 Hz, 1H), 6.68 (dd, J = 7.5, 7.5 Hz, 1H), 6.54 (d, J = 7.5 Hz, 1H), 4.54 (d, J = 15.5 Hz, 1H), 4.07 (d, J = 15.5 Hz, 1H), 3.43 (s, 3H), 2.15 (s, 3H)
18. R. Mezencev, J. Mojzis, M. Pilatova, and P. Kutschy Neoplasma 50 2003 239 245
19. 1H NMR signals of TFAE obscure the signals of the compounds under study, perdeuterated TFAE can be prepared, see: J. Gil, and A. Virgili J. Org. Chem. 64 1999 7277 7280