Total assignment of the proton and carbon NMR spectra of the alkaloid quindoline - utilization of HMQC-TOCSY to indirectly establish protonated carbon-protonated carbon connectivities

作者: T. D. Spitzer , R. C. Crouch , G. E. Martin , M. H. M. Sharaf , Jr. Schiff

DOI: 10.1002/JHET.5570280850

关键词:

摘要: The reisolation of the indoloquinoline alkaloid quindoline (also known as norcryptolepine) from Cryptolepis sanguinolenta is reported. structure was unequivocally confirmed by two-dimensional nmr methods; proton and carbon spectra were assigned for first time. Because congestion in spectrum HMQC-TOCSY used an alternative to more familiar COSY experiment. In addition establishing proton-proton connectivities, affords added benefit providing, indirect sense, connectivity information between protonated carbons.

参考文章(7)
Laura Lerner, Ad Bax, Sensitivity-enhanced two-dimensional heteronuclear relayed coherence transfer NMR spectroscopy Journal of Magnetic Resonance. ,vol. 69, pp. 375- 380 ,(1986) , 10.1016/0022-2364(86)90091-0
Ad Bax, Sankaran Subramanian, Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy Journal of Magnetic Resonance. ,vol. 67, pp. 565- 569 ,(1986) , 10.1016/0022-2364(86)90395-1
Seth Ablordeppey, Charles Hufford, Ronald Borne, Daniel Dwuma-Badu, 1H-NMR and 13C-NMR assignments of cryptolepine, a 3:4-benz-δ-carboline derivative isolated from Cryptolepis sanguinolenta. Planta Medica. ,vol. 56, pp. 416- 417 ,(1990) , 10.1055/S-2006-960998
Daniel Dwuma-Badu, John S.K. Ayim, Nicholas I.Y. Fiagbe, Joseph E. Knapp, Paul L. Schiff, David J. Slatkin, Constituents of West African Medicinal Plants XX: Quindoline from Cryptolepis sanguinolenta Journal of Pharmaceutical Sciences. ,vol. 67, pp. 433- 434 ,(1978) , 10.1002/JPS.2600670350
Ad Bax, Ray Freeman, Stewart P. Kempsell, Natural abundance carbon-13-carbon-13 coupling observed via double-quantum coherence Journal of the American Chemical Society. ,vol. 102, pp. 4849- 4851 ,(1980) , 10.1021/JA00534A056
Gary E. Martin, Ronald C. Crouch, INVERSE-DETECTED TWO-DIMENSIONAL NMR METHODS : APPLICATIONS IN NATURAL PRODUCTS CHEMISTRY Journal of Natural Products. ,vol. 54, pp. 1- 70 ,(1991) , 10.1021/NP50073A001
Albert N. Tackie, Maged H. M. Sharaf, Paul L. Schiff, Gilbert L. Boye, Ronald C. Crouch, Gary E. Martin, Assignment of the proton and carbon NMR spectra of the indoloquinoline alkaloid cryptolepine Journal of Heterocyclic Chemistry. ,vol. 28, pp. 1429- 1435 ,(1991) , 10.1002/JHET.5570280540