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Volumn 44, Issue 32, 2003, Pages 6017-6020

Preparation of cruciferous phytoalexin related metabolites, (-)-dioxibrassinin and (-)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD)

Author keywords

Dioxibrassinin; Dioxindole; Phytoalexin; Tertiary alcohol; VCD

Indexed keywords

3 CYANOMETHYL 3 HYDROXYOXINDOLE; ANTIFUNGAL AGENT; DIOXIBRASSININ; ISATIN; PHYTOALEXIN; UNCLASSIFIED DRUG;

EID: 0038644197     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01513-2     Document Type: Article
Times cited : (46)

References (25)
  • 5
    • 0000354617 scopus 로고    scopus 로고
    • Theologis A., et al. Nature. 408:2000;796.
    • (2000) Nature , vol.408 , pp. 796
    • Theologis, A.1
  • 12
    • 85031146023 scopus 로고    scopus 로고
    • Dukor, R. K.; Nafie, L. A. Encyclopedia of Analytical Chemistry; Vibrational Optical Activity of Pharmaceuticals and Biomolecules. John Wiley & Son: Chichester, 2000; p. 662 Nafie, L. A.; Freedman, T. B. Circular Dichroism, 2nd ed.; Vibrational optical activity theory, 2000; p. 97 Keiderling, T. A. Circular Dichroism, 2nd ed.; Peptide and protein conformational studies with vibrational circular dichroism and related spectroscopies, 2000; p. 621.
  • 15
    • 85031151493 scopus 로고    scopus 로고
    • note
    • D +50° (MeOH; c 1.0).
  • 17
    • 85031158074 scopus 로고    scopus 로고
    • -1 width. The sum of Boltzmann weights of conformers using in the last step covers more than 90% of those of all conformers
    • -1 width. The sum of Boltzmann weights of conformers using in the last step covers more than 90% of those of all conformers.
  • 19
    • 85031150376 scopus 로고    scopus 로고
    • note
    • -1), the VCD bands of compounds 2 and 4 showed moderate agreement between the observed and calculated IR and VCD spectra. However, some bands of 1 did not agree, probably, it may be attributed to the complexity of the dithiocarbamate side chain of 1 .
  • 25
    • 85031145713 scopus 로고    scopus 로고
    • note
    • Cyclization of (S)-(-)-1 (99% ee) by thionyl chloride gave partially racemized (R)- (+)-3 (36% ee).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.