메뉴 건너뛰기




Volumn 22, Issue 2, 2010, Pages 234-241

Absolute configuration determination and conformational analysis of (-)-(3s,6s)-3α,6β-diacetoxytropane using vibrational circular dichroism and DFT techniques

Author keywords

Absolute configuration; Conformational distribution; Tropane alkaloids; VCD

Indexed keywords

TROPANE DERIVATIVE;

EID: 74749102945     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20734     Document Type: Article
Times cited : (26)

References (24)
  • 1
    • 84979978581 scopus 로고
    • The alkaloids
    • Cordell GA, editor, New York: Academic Press;
    • Lounasmaa M, Tamminen T. The alkaloids. In: Cordell GA, editor. The tropane alkaloids, Vol. 44. New York: Academic Press; 1993. p 1-114.
    • (1993) The tropane alkaloids , vol.44 , pp. 1-114
    • Lounasmaa, M.1    Tamminen, T.2
  • 2
    • 0033775563 scopus 로고    scopus 로고
    • Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids
    • O'Hagan D. Pyrrole, pyrrolidine, pyridine, piperidine and tropane alkaloids. Nat Prod Rep 2000;17:435-446.
    • (2000) Nat Prod Rep , vol.17 , pp. 435-446
    • O'Hagan, D.1
  • 3
    • 0031463959 scopus 로고    scopus 로고
    • Pyrrole, pyrrolidine, pyridine, piperidine, azepine and tropane alkaloids
    • O'Hagan D. Pyrrole, pyrrolidine, pyridine, piperidine, azepine and tropane alkaloids. Nat Prod Rep 1997;14:637-651.
    • (1997) Nat Prod Rep , vol.14 , pp. 637-651
    • O'Hagan, D.1
  • 6
    • 33750002013 scopus 로고    scopus 로고
    • Absolute configuration of natural diastereoisomers of 6b-hydroxyhyoscyamine by vibrational circular dichroism
    • Muñoz MA, Muñoz O, Joseph-Nathan P. Absolute configuration of natural diastereoisomers of 6b-hydroxyhyoscyamine by vibrational circular dichroism. J Nat Prod 2006;69:1335-1340.
    • (2006) J Nat Prod , vol.69 , pp. 1335-1340
    • Muñoz, M.A.1    Muñoz, O.2    Joseph-Nathan, P.3
  • 7
    • 37349012570 scopus 로고    scopus 로고
    • Absolute configuration of tropane alkaloids bearing two α,β-unsaturated ester functions using electronic CD spectroscopy: Application to (R,R)-trans-3- hydroxysenecioyloxy-6-senecioyloxytropane
    • Humam M, Christen P, Muñoz O, Hostettmann K, Jeannerat D. Absolute configuration of tropane alkaloids bearing two α,β-unsaturated ester functions using electronic CD spectroscopy: application to (R,R)-trans-3- hydroxysenecioyloxy-6-senecioyloxytropane. Chirality 2008;20:20-25.
    • (2008) Chirality , vol.20 , pp. 20-25
    • Humam, M.1    Christen, P.2    Muñoz, O.3    Hostettmann, K.4    Jeannerat, D.5
  • 8
    • 0001120062 scopus 로고
    • Variation in tropane alkaloid accumulation within the Solanaceae and strategies for its exploitation
    • Parr AJ, Payne J, Eagle J, Chapman BT, Robins RJ, Rhodes MJC. Variation in tropane alkaloid accumulation within the Solanaceae and strategies for its exploitation. Phytochemistry 1990;29:2545-2550.
    • (1990) Phytochemistry , vol.29 , pp. 2545-2550
    • Parr, A.J.1    Payne, J.2    Eagle, J.3    Chapman, B.T.4    Robins, R.J.5    Rhodes, M.J.C.6
  • 9
    • 0242322522 scopus 로고    scopus 로고
    • Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism
    • Freedman TB, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003;15:743-758.
    • (2003) Chirality , vol.15 , pp. 743-758
    • Freedman, T.B.1    Cao, X.2    Dukor, R.K.3    Nafie, L.A.4
  • 10
    • 77954027135 scopus 로고    scopus 로고
    • Vibrational circular dichroism: A new tool for the solutionstate determination of the structure and absolute configuration of chiral natural product molecules
    • Nafie LA. Vibrational circular dichroism: a new tool for the solutionstate determination of the structure and absolute configuration of chiral natural product molecules. Nat Prod Commun 2008;3:451-466.
    • (2008) Nat Prod Commun , vol.3 , pp. 451-466
    • Nafie, L.A.1
  • 12
    • 47549117785 scopus 로고    scopus 로고
    • Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
    • Cerda-García-Rojas CM, Catalán CAN, Muro AC, Joseph-Nathan P. Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia. J Nat Prod 2008;71:967-971.
    • (2008) J Nat Prod , vol.71 , pp. 967-971
    • Cerda-García-Rojas, C.M.1    Catalán, C.A.N.2    Muro, A.C.3    Joseph-Nathan, P.4
  • 13
    • 48349127385 scopus 로고    scopus 로고
    • Absolute configuration of eremophilanoids by vibrational circular dichroism
    • Burgueño-Tapia E, Joseph-Nathan P. Absolute configuration of eremophilanoids by vibrational circular dichroism. Phytochemistry 2008;69: 2251-2256.
    • (2008) Phytochemistry , vol.69 , pp. 2251-2256
    • Burgueño-Tapia, E.1    Joseph-Nathan, P.2
  • 14
    • 74749098691 scopus 로고    scopus 로고
    • Spartan '04. Wavefunction: Irvine, CA, 2004.
    • Spartan '04. Wavefunction: Irvine, CA, 2004.
  • 15
    • 74749092806 scopus 로고    scopus 로고
    • Gaussian 03W. Gaussian Inc.: Pittsburgh, PE, 2003.
    • Gaussian 03W. Gaussian Inc.: Pittsburgh, PE, 2003.
  • 16
    • 74749092937 scopus 로고    scopus 로고
    • PeakFit v4.12 for Windows, SeaSolve Software Inc.: San Jose, CA, 2003.
    • PeakFit v4.12 for Windows, SeaSolve Software Inc.: San Jose, CA, 2003.
  • 17
    • 0000638081 scopus 로고
    • 7β-Hydroxyhyoscyamine from Duboisia myoporoides-D. leichhardtii hybrid and Hyoscyamus albus
    • Ishimaru K, Shimomura K. 7β-Hydroxyhyoscyamine from Duboisia myoporoides-D. leichhardtii hybrid and Hyoscyamus albus. Phytochemistry 1989;28:3507-3509.
    • (1989) Phytochemistry , vol.28 , pp. 3507-3509
    • Ishimaru, K.1    Shimomura, K.2
  • 18
    • 0032783951 scopus 로고    scopus 로고
    • Conformational pseudopolymorphism and solidstate CPMAS NMR studies for determination of solvent-dependent solution-state conformational preferences for (-)-scopolamine hydrobromide/ hydrochloride salts
    • Glaser R, Shiftan D. Conformational pseudopolymorphism and solidstate CPMAS NMR studies for determination of solvent-dependent solution-state conformational preferences for (-)-scopolamine hydrobromide/ hydrochloride salts. J Org Chem 1999;64:9217-9224.
    • (1999) J Org Chem , vol.64 , pp. 9217-9224
    • Glaser, R.1    Shiftan, D.2
  • 19
    • 0013688948 scopus 로고    scopus 로고
    • Scopolamine and antropine Nmethyl diastereomer stability. Ab initio calculations on O-formylscopine and O-formyltropine model compounds
    • Glaser R, Khutorsky V, Shoken M. Scopolamine and antropine Nmethyl diastereomer stability. Ab initio calculations on O-formylscopine and O-formyltropine model compounds. Struct Chem 1997;8:319-329.
    • (1997) Struct Chem , vol.8 , pp. 319-329
    • Glaser, R.1    Khutorsky, V.2    Shoken, M.3
  • 20
    • 33845280718 scopus 로고
    • Stereochemistry of the N-methyl group in salts of tropane alkaloids
    • Glaser R, Peng Q-J, Perlin AS. Stereochemistry of the N-methyl group in salts of tropane alkaloids. J Org Chem 1988;52:2172-2180.
    • (1988) J Org Chem , vol.52 , pp. 2172-2180
    • Glaser, R.1    Peng, Q.-J.2    Perlin, A.S.3
  • 21
    • 84989141797 scopus 로고
    • Spectral reassignment and structure elucidation of scopolamine free base through twodimensional NMR techniques
    • Sarazin C, Goethals G, Séguin J-P, Barbotin J-N. Spectral reassignment and structure elucidation of scopolamine free base through twodimensional NMR techniques. Magn Reson Chem 1991;29:291-300.
    • (1991) Magn Reson Chem , vol.29 , pp. 291-300
    • Sarazin, C.1    Goethals, G.2    Séguin, J.-P.3    Barbotin, J.-N.4
  • 22
    • 34247598222 scopus 로고    scopus 로고
    • Determination of the absolute configuration of natural products via density functional theory calculations of vibracional circular dichroism, electronic circular dichroism, and optical rotation: The iridoids plumericin and isoplumericin
    • Stephens PJ, Pan JJ, Devlin FJ, Krohn K, Kurtán T. Determination of the absolute configuration of natural products via density functional theory calculations of vibracional circular dichroism, electronic circular dichroism, and optical rotation: the iridoids plumericin and isoplumericin. J Org Chem 2007;72:3521-3536.
    • (2007) J Org Chem , vol.72 , pp. 3521-3536
    • Stephens, P.J.1    Pan, J.J.2    Devlin, F.J.3    Krohn, K.4    Kurtán, T.5
  • 23
    • 45149135283 scopus 로고    scopus 로고
    • Solvent effects on IR and VCD spectra of natural products: An experimental and theoretical VCD study of pulegone
    • Debie E, Bultinck P, Herrebout W, van der Veken B. Solvent effects on IR and VCD spectra of natural products: an experimental and theoretical VCD study of pulegone. Phys Chem Chem Phys 2008;10:3498-3508.
    • (2008) Phys Chem Chem Phys , vol.10 , pp. 3498-3508
    • Debie, E.1    Bultinck, P.2    Herrebout, W.3    van der Veken, B.4
  • 24
    • 49349099121 scopus 로고    scopus 로고
    • Effects of complex formation on vibrational circular dichroism spectra
    • Nicu VP, Neugebauer J, Baerends EJ. Effects of complex formation on vibrational circular dichroism spectra. J Phys Chem A 2008;112: 6978-6991.
    • (2008) J Phys Chem A , vol.112 , pp. 6978-6991
    • Nicu, V.P.1    Neugebauer, J.2    Baerends, E.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.