Determination of absolute configuration of natural products: Theoretical calculation of electronic circular dichroism as a tool

Current Organic Chemistry

Volumn 14, Issue 16, 2010, Pages 1678-1697

  Li, Xing Cong ^a,b   Ferreira, Daneel ^a,b   Ding, Yuanqing ^a  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Absolute configuration; Electronic circular dichroism; Natural products; TDDFT; Theoretical calculation

Indexed keywords

CHROMOPHORES; CIRCULAR DICHROISM SPECTROSCOPY; DENSITY FUNCTIONAL THEORY; DICHROISM; LIPIDS; MOLECULAR ORBITALS; STEREOCHEMISTRY;

ABSOLUTE CONFIGURATION; CIRCULAR DICHROISM SPECTRA; CIRCULAR DICHROISM SPECTRUMS; ELECTRONIC CIRCULAR DICHROISM; FLAVONOID; NATURAL PRODUCTS; STRUCTURE ELUCIDATION; THEORETICAL CALCULATIONS; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TIME DEPENDENT DENSITY FUNCTIONAL THEORY CALCULATIONS;

FLAVONOIDS;

EID: 78649918714     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210792927717     Document Type: Article

References (97)

1. Mechlinski, W.; Schaffner, C.P.; Ganis, P.; Avitabile, G. Structure and absolute configuration of the polyene macrolide antibiotic amphotericin B. Tetrahedron Lett., 1970, 44, 3873-3876.
2. Flack, H. D. On enantiomorph-polarity estimation. Acta Crystallogr. Sect. A, 39, 1983, 876-881.
3. Flack, H. D.; Bernardinelli, G. Reporting and evaluating absolutestructure and absolute-configuration determinations. J. Appl. Crystallogr., 2000, 33, 1143-1148.
4. Hooft, R. W. W.; Straver, L. H.; Spek, A. L. Determination of absolute structure using Bayesian statistics on Bijvoet differences. J. Appl. Crystallogr., 2008, 41, 96-103.
5. Kamel, H. N.; Ding, Y. Q.; Li, X. C.; Ferreira, D.; Fronczek, F. R.; Slattery, M. Beyond polymaxenolide: cembrane-Africanane terpenoids from the hybrid soft coral Sinularia maxima x S. polydactyla J. Nat. Prod., 2009, 72, 900-905.
6. Fu, X.; Li, X.-C.; Smillie T. A.; Carvalho, P.; Mabusela, W.; Syce, J.; Johnson, Q.; Folk, W.; Avery, M. A.; Khan, I. A. Cycloartane glycosides from Sutherlandia frutescens. J. Nat. Prod., 2008, 71, 1749-1753.
7. Nicolaou, K. C.; Daines, R. A.; Ogawa, Y.; Chakraborty, T. K. J. Total synthesis of amphotericin B. 3. The final stages. J. Am. Chem. Soc., 1988, 110, 4696-4705.
8. Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H.; Nantermet, P. G.; Guy, R. K.; Claiborne, C. F.; Renaud, J.; Couladouros, E. A.; Paulvannan, K.; Sorensen, E. J. Total synthesis of taxol. Nature, 1994, 367, 630-634.
9. Seco, J. M.; Quiñoá, E.; Riguera, R. The assignment of absolute configuration by NMR. Chem. Rev., 2004, 104, 17-117.
10. Dale, J. A.; Mosher, H. S. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α- trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc., 1973, 95, 512-519.
11. Adams, C. M.; Indranath Ghosh, I.; Kishi, Y. Validation of lanthanide chiral shift reagents for determination of absolute configuration: total synthesis of glisoprenin A. Org. Lett., 2004, 6, 4723-4726.
12. Buist, P. H.; Dale Marecak, D.; Holland, H. L.; Brown, F. M. (S)-α- Methoxyphenyl acetic acid: a new NMR chiral shift reagent for the stereochemical analysis of sulfoxides. Tetrahedron Asymmetry 1995, 6, 7-10.
13. B'Hymer, C.; Montes-Bayon, M.; Caruso, J. A. Marfey's reagent: Past, present, and future uses of 1-fluoro-2,4-dinitrophenyl-5-L-alanine amide. J. Separ. Sci. 2003, 26, 7-19.
14. Hara, S.; Okabe, H.; Mihashi, K. Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylates. Chem. Pharm. Bull., 1987, 35, 501-506.
15. Tanaka, T.; Nakashima, T.; Ueda, T.; Tomii, K.; Kouno, I. Facile discrimination of aldose enantiomers by reversed-phase HPLC. Chem. Pharm. Bull., 2007, 55, 899-901.
16. Klyne, W. The configuration of the anomeric carbon atoms in some cardiac glycosides. Biochem. J., 1950, 47, xli-xlii.
17. Barton, D. H. R. Application of the method of molecular rotation differences to steroids. I. Naturally occurring sterols and their simple derivatives. J. Chem. Soc., 1945, 813-819.
18. Moffitt, W.; Woodward, R. B.; Moscowitz, A.; Klyne, W.; Djerassi, C. Structure and the optical rotatory dispersion of saturated ketones. J. Am. Chem. Soc., 1961, 83, 4013-4018.
19. Moscowitz, A.; Mislow, K.; Glass, M. A. W.; Djerassi, C. Optical rotatory dispersion studies. LXVI. Optical rotatory dispersion associated with dissymmetric nonconjugated chromophores. An extension of the octant rule. J. Am. Chem. Soc., 1962, 84, 1945-1955.
20. DeAngelis, G. G.; Wildman, W. C. Circular dichroism studies. I. A quadrant rule for the optically active aromatic chromophore in rigid polycyclic systems. Tetrahedron, 1969, 25, 5099-5112.
21. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
22. Harada, N.; Kohori, J.; Uda, H.; Toriumi, K. Synthesis, absolute stereochemistry, and circular dichroism of chiral 1,8a-dihydroazulene derivatives. J. Org. Chem., 1989, 54, 1820-1826.
23. Harada, N.; Uda, H.; Kobayashi, M.; Shimizu, N.; Kitagawa, I. Absolute stereochemistry of the halenaquinol family, marine natural products with a novel pentacyclic skeleton, as determined by the theoretical calculation of circular dichroism spectra. J. Am. Chem. Soc., 1989, 111, 5668-5674.
24. Ferris, J. P.; Boyce, C. B.; Briner, R. C.; Weiss, U.; Qureshi, I. H.; Sharpless, N. E. Lythraceae alkaloids. X. Assignment of absolute stereochemistries on the basis of chiraloptical effects. J. Am. Chem. Soc., 1971, 93, 2963-2968.
25. Slade, D.; Ferreira, D.; Marais, J. P. J. Circular dichroism, a powerful tool for the assessment of absolute configuration of flavonoids. Phytochemistry, 2005, 66, 2177-2215.
26. Rodger, A.; Nordén, B. Circular Dichroism and Linear Dichroism, Oxford University Press: Oxford, UK, 1997.
27. Fasman, G. D. Circular Dichroism and the Conformational Analysis of Biomolecules, Plenum Press: New York, 1996.
28. Berova, N.; Nakanishi, K. Circular Dichroism Principles and Applications; Berova, N.; Nakanishi, K.; Woody, R. W. Eds.; John Wiley & Sons: New York, 2000; Chapter 12, pp. 337-382.
29. Berova, N.; Bari, L. D.; Pescitelli, G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem. Soc. Rev., 2007, 36, 914-931.
30. Gaffield, W. Circular dichroism, optical rotatory dispersion, and absolute configuration of flavanones, 3-hydroxyflavanones, and their glycosides. Determination of aglycone chirality in flavanone glycosides. Tetrahedron, 1970, 26, 4093-4108.
31. Diedrich, C.; Grimme, S. Systematic investigation of modern quantum chemical methods to predict electronic circular dichroism spectra. J. Phys. Chem. A, 2003, 107, 2524-2539.
32. Stephens, P. J.; McCann, D. M.; Butkus, E.; Stoncius, S.; Cheeseman, J. R.; Frisch, M. J. Determination of absolute configuration using concerted ab initio DFT calculations of electronic circular dichroism and optical rotation: bicyclo[3.3.1]nonane diones. J. Org. Chem., 2004, 69, 1948-1958.
33. Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. Determination of the absolute configuration of [3(2)](1,4)barrelenophanedicarbonitrile using concerted time-dependent density functional theory calculations of optical rotation and electronic circular dichroism. J. Am. Chem. Soc., 2004, 126, 7514-7521.
34. Schühly, W.; Crochett, S. L.; Fabian, W. M. F. Hyperolactone C: Determination of its absolute configuration by comparison of experimental and calculated CD spectra. Chirality, 2005, 17, 250-256.
35. McCann, D. M.; Stephens, P. J. Determination of absolute configuration using density functional theory calculations of optical rotation and electronic circular dichroism: chiral alkenes. J. Org. Chem., 2006, 71, 6074-6098.
36. Crawford, T. D.; Tam, M. C.; Abrams, M. L. The current state of ab initio calculations of optical rotation and electronic circular dichroism spectra. J. Phys. Chem. A, 2007, 111, 12057-12068.
37. Stephens, P. J.; Devlin, F. J.; Gasparrini, F.; Ciogli, A.; Spinelli, D.; Cosimelli, B. Determination of the absolute configuration of a chiral oxadiazol-3-one calcium channel blocker, resolved using chiral chromatography, via concerted density functional theory calculations of its vibrational circular dichroism, electronic circular dichroism, and optical rotation. J. Org. Chem., 2007, 72, 4707-4715.
38. Ding, Y.; Li, X.-C.; Ferreira, D. Theoretical calculation of electronic circular dichroism of the rotationally restricted 3,8''-biflavonoid morelloflavone. J. Org. Chem., 2007, 72, 9010-9017.
39. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. The assignment of absolute stereostructures through quantum chem. circular dichroism calculations. Eur. J. Org. Chem., 2009, 2717-2727.
40. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. Calculation of optical rotation using density functional theory. J. Phys. Chem. A, 2001, 105, 5356-5371.
41. Polavarapu, P. L. Optical rotation: recent advances in determining the absolute configuration. Chirality, 2002, 14, 768-781.
42. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. Ab initio prediction of optical rotation: comparison of density functional theory and Hartree- Fock methods for three 2,7,8- trioxabicyclo[3.2.1]octanes. Chirality, 2002, 14, 288-296.
43. Stephens, P. J.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J.; Bortolini, O.; Besse, P. Determination of absolute configuration using ab initio calculation of optical rotation. Chirality, 2003, 15, S57-S64.
44. McCann, D. M.; Stephens, P. J.; Cheeseman, J. R. Determination of absolute configuration using density functional theory calculation of optical rotation: chiral alkanes. J. Org. Chem., 2004, 69, 8709-8717.
45. Giorgio, E.; Roje, M.; Tanaka, K.; Hamersak, Z.; Sunjik, V.; Nakanishi, K.; Rosini, C.; Berova, N. Determination of the absolute configuration of flexible molecules by ab initio ORD calculations: a case study with cytoxazones and isocytoxazones. J. Org. Chem., 2005, 70, 6557-6563.
46. Stephens, P. J.; Pan, J. J.; Devlin, F. J.; Cheeseman, J. R. Determination of the absolute configurations of natural products using TDDFT optical rotation calculations: the iridoid oruwacin. J. Nat. Prod., 2008, 71, 285-288.
47. Aamouche, A.; Devlin, F. J.; Stephens, P.J. Determination of absolute configuration using circular dichroism: Troger's base revisited using vibrational circular dichroism. Chem. Commun., 1999, 361-362.
48. Aamouche, A.; Devlin, F. J.; Stephens, P. J. Structure, vibrational absorption and circular dichroism spectra, and absolute configuration of Troger's base. J. Am. Chem. Soc., 2000, 122, 2346-2354.
49. Devlin, F. J.; Stephens, P. J.; Oesterle, C.; Wiberg, K. B.; Cheeseman, J. R.; Frisch, M. J. Configurational and conformational analysis of chiral molecules using IR and VCD spectroscopies: spiropentylcarboxylic acid methyl ester and spiropentyl acetate. J. Org. Chem., 2002, 67, 8090-8096.
50. Freedman, T. B.; Cao, X.; Dukor, R. K.; Nafie, L. A. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003, 15, 743-758.
51. Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Flood, T. C.; Butkus, E.; Stoncius, S.; Cheeseman, J. R. Determination of molecular structure using vibrational circular dichroism spectroscopy: the keto-lactone product of Baeyer-Villiger oxidation of (+)-(1R,5S)-bicyclo[3.3.1]nonane-2,7-dione. J. Org. Chem., 2005, 70, 3903-3913.
52. Carosati, E.; Cruciani, G.; Chiarini, A.; Budriesi, R.; Ioan, P.; Spisani, R.; Spinelli, D.; Cosimelli, B.; Fusi, F.; Frosini, M.; Matucci, R.; Gasparrini, F.; Ciogli, A.; Stephens, P. J.; Devlin, F. J. Calcium channel antagonists discovered by a multidisciplinary approach. J. Med. Chem., 2006, 49, 5206-5216.
53. Monde, K.; Taniguchi, T.; Miura, M.; Vairappan, C. S.; Suzuki, M. Absolute configurations of endoperoxides determined by vibrational circular dichroism (VCD). Tetrahedron Lett., 2006, 47, 4389-4392.
54. Cerda-García-Rojas, C. M.; Catalán, C. A. N.; Muro, A. C.; Joseph-Nathan, P. Vibrational circular dichroism of Africanane and lippifoliane sesquiterpenes from Lippia integrifolia. J. Nat. Prod., 2008, 71, 967-971.
55. Crawford, T. D.; Tam, M. C.; Abrams, M. L. The problematic case of (S)- methylthiirane: electronic circular dichroism spectra and optical rotatory dispersion. Mol. Phys., 2007, 105, 2607-2617.
56. Skomorowski, W.; Pecul, M.; Salek, P.; Helgaker, T. Electronic circular dichroism of disulphide bridge: ab initio quantum-chemical calculations. J. Chem. Phys., 2007, 127, 085102/1-085102/8.
57. Pecul, M.; Ruud, K. The ab initio calculation of optical rotation and electronic circular dichroism. Adv. Quant. Chem. 2005, 50, 185-212.
58. Kwit, M.; Sharma, N.D.; Boyd, D. R.; Gawronski, J. Absolute configuration of conformationally flexible cis-dihydrodiol metabolites by the method of confrontation of experimental and calculated electronic CD spectra and optical rotations. Chem-Eur. J., 2007, 13, 5812-5821.
59. Mori, T.; Inoue, Y.; Grimme, S. Quantum chemical study on the circular dichroism spectra and specific rotation of donor-acceptor cyclophanes. J. Phys. Chem. A, 2007, 111, 7995-8006.
60. Giorgio, E.; Tanaka, K.; Ding, W.; Krishnamurthy, G.; Pitts, K.; Ellestad, G. A.; Rosini, C.; Berova, N. Theoretical simulation of the electronic circular dichroism spectrum of calicheamicin. Bioorg. Med. Chem., 2005, 13, 5072-5079.
61. Gawronski, J. K.; Kwit, M.; Boyd, D. R.; Sharma, N. D.; Malone, J. F.; Drake, A. F. Absolute configuration, conformation, and circular dichroism of monocyclic arene dihydrodiol metabolites: it is all due to the heteroatom substituents. J. Am. Chem. Soc., 2005, 127, 4308-4319.
62. Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Smith, A. B., III. Determination of the absolute configurations of natural products via density functional theory calculations of optical rotation, electronic circular dichroism, and vibrational circular dichroism: the cytotoxic sesquiterpene natural products quadrone, suberosenone, suberosanone, and suberosenol A acetate. J. Nat. Prod., 2006, 69, 1055-1064.
63. Stephens, P. J.; Pan, J. J.; Devlin, F. J.; Krohn, K.; Kurtan, T. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: the iridoids plumericin and isoplumericin. J. Org. Chem., 2007, 72, 3521-3536.
64. Stephens, P.J.; Pan, J. J.; Devlin, F. J.; Urbanova, M.; Hajicek, J. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism and optical rotation: the schizozygane alkaloid schizozygine. J. Org. Chem., 2007, 72, 2508-2524.
65. Hussain, H.; Krohn, K.; Floerke, U.; Schulz, B.; Draeger, S.; Pescitelli, G.; Antus, S.; Kurtán, T. Absolute configurations of globosuxanthone A and secondary metabolites from Microdiplodia sp. - a novel solid-state CD/TDDFT approach. Eur. J. Org. Chem., 2007, 292-295.
66. Stephens, P. J.; Pan, J.-J.; Devlin, F. J.; Urbanova, M.; Julinek, O.; Hajicek, J. Determination of the absolute configurations of natural products via density functional theory calculations of vibrational circular dichroism, electronic circular dichroism, and optical rotation: the iso-schizozygane alkaloids isoschizogaline and isoschizogamine. Chirality, 2008, 20, 454-470.
67. Bringmann, G.; Gulder, T. A. M.; Reichert, M.; Gulder, T. The online assignment of the absolute configuration of natural products: HPLC-CD in combination with quantum chemical CD calculations. Chirality, 2008, 20, 628-642.
68. Grkovic, T.; Ding, Y.; Li, X. C.; Webb, V. L.; Ferreira, D.; Copp, B. R. Enantiomeric discorhabdin alkaloids and establishment of their absolute configurations using theoretical calculations of electronic circular dichroism spectra. J. Org. Chem., 2008, 73, 9133-9136.
69. Ross, S. A.; Rodriguez-Guzman, R.; Radwan, M. M.; Jacob, M. R.; Ding, Y. Q.; Li, X. C., Ferreira, D.; Manly, S. P.; Sorocenol, G. H. Sorocenols G and Hanti-MRSA oxygen heterocyclic Diels-Alder-type adducts from Sorocea muriculata roots. J. Nat. Prod., 2008, 71, 1764-1767.
70. Ding, Y.; Li, X. C.; Ferreira, D. Theoretical calculation of electronic circular dichroism of a hexahydroxydiphenoyl-containing flavanone glycoside. J. Nat. Prod., 2009, 72, 327-335.
71. Shukla, Y. J.; Pawar, R. S.; Ding, Y.; Li, X. C.; Ferreira, D.; Khan, I. A. Pregnane glycosides from Hoodia gordonii. Phytochemistry, 2009, 70, 675-683.
72. Yang, X.-W.; Ding, Y.; Li, X.-C.; Ferreira, D.; Shen, Y.-H.; Li, S. M.; Wang, N.; Zhang, W.-D. Cycloabiesesquine A, a unique sesquiterpenoid from Abies delavayi. Chem. Commun., 2009, 25, 3771-3773.
73. Li, J.; Ding, Y.; Li, X.-C.; Ferreira, D.; Khan, S. I.; Smillie, T. J.; Khan, I. A. Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora. J. Nat. Prod., 2009, 72, 983-987.
74. Taniguchi, T.; Martin, C. L.; Monde, K.; Nakanishi, K.; Berova, N.; Overman L.E. Absolute configuration of actinophyllic acid as determined through chiroptical data. J. Nat. Prod., 2009, 72, 430-432.
75. Gan, L.-S.; Zheng, Y.-L.; Mo, J.-X.; Liu, X.; Li, X.-H.; Zhou, C.-X. Sesquiterpene lactones from the root tubers of Lindera aggregata. J. Nat. Prod., 2009, 72, 1497-1501.
76. Petrovic, A. G.; He, J.; Polavarapu, P. L.; Xiao, L. S.; Armstrong, D. W. Absolute configuration and predominant conformations of 1,1-dimethyl-2- phenylethyl phenyl sulfoxide. Org. Biomol. Chem., 2005, 3, 1977-1981.
77. Claps, M.; Parrinello, N.; Saa, C.; Varela, J. A.; Caccamese, S.; Rosini, C. Assignment of the absolute configuration of (+)-5,5',6,6'-tetrahydro-7,7'- spiro[7H-cyclopenta[b]pyridine], a new inherently chiral spiropyridine, by a nonempirical analysis of its circular dichroism spectrum. Tetrahedron Asymmetry 2006, 17, 1387-1393.
78. Giorgio, E.; Tanaka, K.; Verotta, L.; Nakanishi, K.; Berova, N.; Rosini, C. Determination of the absolute configurations of flexible molecules: synthesis and theoretical simulation of electronic circular dichroism/optical rotation of some pyrrolo[2,3-b]indoline alkaloids - a case study. Chirality, 2007, 19, 434-445.
79. Tanaka, T.; Oelgemoller, M.; Fukul, K.; Aoki, F.; Mori, T.; Ohno, T.; Inoue, Y. Unusual CD couplet pattern observed for the pi*←n transition of enantiopure (Z)-8-methoxy-4-cyclooctenone: an experimental and theoretical study by electronic and vibrational circular dichroism spectroscopy and density functional theory calculation. Chirality, 2007, 19, 415-427.
80. Ding, S.; Jia, L.; Durandin, A.; Crean, C.; Kolbanovskiy, A.; Shafirovich, V.; Broyde, S.; Geacintov, N. E. Absolute configurations of spiroiminodihydantoin and allantoin stereoisomers: comparison of computed and measured electronic circular dichroism spectra. Chem. Res. Toxicol., 2009, 22, 1189-1193.
81. Bicker, W.; Kacprzak, K.; Kwit, M.; Laemmerhofer, M.; Gawronski, J.; Lindner, W. Assignment of absolute configurations of permethrin and its synthon 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid by electronic circular dichroism, optical rotation, and X-ray crystallography. Tetrahedron Asymmetry, 2009, 20, 1027-1035.
82. Sybyl 8.0; Tripos Inc., www.tripos.com.
83. Spartan 02; Wavefunction, Inc.; www.wafefun.com.
84. Gaussian03, Gaussian, Inc., www.gaussian.com.
85. Pecul, M.; Ruud, K.; Helgaker, T. Density functional theory calculation of electronic circular dichroism using London orbitals. Chem. Phys. Lett., 2004, 388, 110-119.
86. Klamt, A.; Schürmann, G. COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc., Perkin Trans. 2, 1993, 2, 799-805.
87. Klamt, A. Conductor-like screening model for real solvents: a new approach to the quantitative calculation of solvation phenomena. J. Phys. Chem., 1995, 99, 2224-2235.
88. Eckert, F.; Klamt, A. Fast solvent screening via quantum chemistry: COSMO-RS approach. AIChE J., 2002, 48, 369-385.
89. Al-Basheer, W.; Pagni, R. M.; Compton, R. N. Spectroscopic and theoretical investigation of (R)-3-methylcyclopentanone. The effect of solvent and temperature on the distribution of conformers. J. Phys. Chem. A, 2007, 111, 2293-2298.
90. Mori, T.; Inoue, Y.; Grimme, S. Time dependent density functional theory calculations for electronic circular dichroism spectra and optical rotations of conformationally flexible chiral donor-acceptor dyad. J. Org. Chem., 2006, 71, 9797-9806.
91. Caccamese, S.; Caruso, C.; Parrinello, N.; Savarino, A. High-performance liquid chromatographic separation and chiroptical properties of the enantiomers of naringenin and other flavanones. J. Chromatogr. A, 2005, 1076, 155-162.
92. Li, X.-C.; Joshi, A. S.; Tan, B.; ElSohly, H. N.; Walker, L. A.; Zjawiony, J. K.; Ferreira, D. Absolute configuration, conformation, and chiral properties of flavanone-(3-8'')-flavone biflavonoids from Rheedia acuminata. Tetrahedron, 2002, 58, 8709-8717.
93. Duddeck, H.; Snatzke, G.; Yemul, S. S. 13C NMR and CD of some 3,8''- biflavanoids from Garcinia species and of related flavanones. Phytochemistry, 1978, 17, 1369-1373.
94. Li, X.-C.; Jacob, M. R.; Pasco, D. S.; ElSohly, H. N.; Nimrod, A. C.; Walker, L. A.; Clark, A. M. Phenolic compounds from Miconia myriantha inhibiting Candida secreted aspartic proteases. J. Nat. Prod., 2001, 64, 1282-1285.
95. Okuda, T.; Yoshida, T.; Hatano, T.; Koga, T.; Toh, N.; Kuriyama, K. Circular dichroism of hydrolyzable tannins. I. Ellagitannins and gallotannins. Tetrahedron Lett., 1982, 38, 3937-3940.
96. Na, M.; Ding, Y.; Wang, B.; Tekwani, B.L.; Schinazi, R. F.; Franzblau, S.; Kelly, M.; Stone, R.; Li, X.-C.; Ferreira, D.; Hamann, M. T. Anti-infective discorhabdins from a deep-water Alaskan sponge of the genus Latrunculia. J. Nat. Prod., 2010, 73, 383-387.
97. Bringmann G.; Maksimenka K.; Bruhn T.; Reichert M.; Harada T.; Koroda R. Quantum chemical CD calculations of dioncophylline A in the solid state. Tetrahedron, 2009, 65, 5720-5728