Absolute configuration of a rare sesquiterpene: (+)-3-ishwarone

Journal of Natural Products

Volumn 77, Issue 8, 2014, Pages 1881-1886

  Junior, Fernando M S ^a   Covington, Cody L ^b   De Amorim, Mauro B ^a   Velozo, Leosvaldo S M ^a   Kaplan, Maria A C ^a   Polavarapu, Prasad L ^b  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISHWARONE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; 3-ISHWARONE; SESQUITERPENE;

ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; ELECTRONIC DISSYMMETRY FACTOR; NONHUMAN; OPTICAL ROTARY DISPERSION; SPECTROSCOPY; VIBRATIONAL DISSYMMETRY FACTOR; ALGORITHM; BRAZIL; CHEMICAL STRUCTURE; CHEMISTRY; OPTICAL ROTATORY DISPERSION; PEPEROMIA; PLANT; STEREOISOMERISM;

ALGORITHMS; BRAZIL; CIRCULAR DICHROISM; MOLECULAR STRUCTURE; OPTICAL ROTATORY DISPERSION; PEPEROMIA; PLANT COMPONENTS, AERIAL; SESQUITERPENES; STEREOISOMERISM;

EID: 84906658622     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500363e     Document Type: Article

References (25)

1. Li, X.-C.; Ferreira, D.; Ding, Y. Curr. Org. Chem. 2010, 14, 1678-1697
2. Pescitelli, G.; Di Bari, L.; Berova, N. Chem. Soc. Rev. 2011, 40 (9) 4603-4625
3. Autschbach, J.; Nitsch-Velasquez, L.; Rudolph, M. In Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures; Naaman, R.; Beratan, D. N.; Waldeck, D., Eds.; Springer: Berlin, 2011; Vol. 298, pp 1-98.
4. Polavarapu, P. L.; Donahue, E. A.; Shanmugam, G.; Scalmani, G.; Hawkins, E. K.; Rizzo, C.; Ibnusaud, I.; Thomas, G.; Habel, D.; Sebastian, D. J. Phys. Chem. A 2011, 115, 5665-5673
5. Polavarapu, P. L. Chirality 2008, 20, 664-672
6. Crawford, T. D.; Tam, M. C.; Abrams, M. L. J. Phys. Chem. A 2007, 111, 12057-12068
7. Barron, L. D.; Buckingham, A. D. Chem. Phys. Lett. 2010, 492, 199-213
8. Vandenbussche, J.; Bultinck, P.; Przybył, A. K.; Herrebout, W. A. J. Chem. Theory Comput. 2013, 9, 5504-5512
9. Shen, J.; Li, Y.; Vaz, R.; Izumi, H. J. Chem. Theory Comput. 2012, 8, 2762-2768
10. Covington, C. L.; Polavarapu, P. L. J. Phys. Chem. A 2013, 117, 3377-3386
11. Polavarapu, P. L.; Covington, C. L. Chirality 2014, doi: 10.1002/chir.22316 (March).
12. Dos S. Junior, F.; Velozo, L.; De Carvalho, E.; Marques, A.; Borges, R.; Trindade, A.; Dos Santos, M.; De Albuquerque, A.; Costa, F.; Kaplan, M.; De Amorim, M. Molecules 2013, 18, 13520-13529
13. Lago, J. H. G.; Oliveira, A. d.; Guimarães, E. F.; Kato, M. J. J. Braz. Chem. Soc. 2007, 18, 638-642
14. Govindachari, T. R.; Nagarajan, K.; Parthasarathy, P. C. J. Chem. Soc. D 1969, 823a-823a
15. Fraga, B. M. Nat. Prod. Rep. 2013, 30, 1226-1264
16. Lightner, D. A. In Analytical Application of Circular Dichroism; Purdie, N.;; Brittain, H. G., Eds.; Elsevier Science B.V.: Amsterdam, 1994; pp 131-174.
17. Hanwell, M.; Curtis, D.; Lonie, D.; Vandermeersch, T.; Zurek, E.; Hutchison, G. J. Chem. Inf. 2012, 4, 17
18. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
19. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
20. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200-1211
21. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213-222
22. Dunning, T. H. J. Chem. Phys. 1989, 90 (2) 1007-1023
23. Mennucci, B.; Cappelli, C.; Cammi, R.; Tomasi, J. Chirality 2011, 23, 717-729
24. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
25. Covington, C. L.; Polavarapu, P. L. CDSpecTech: Computer programs for calculating similarity measures of comparison between experimental and calculated dissymmetry factors and circular intensity differentials; https://sites.google.com/site/cdspectech1/; 2014.