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

Volumn 19, Issue 6, 2007, Pages 434-445

  Giorgio, Egidio ^a   Tanaka, Katsunori ^b   Verotta, Luisella ^c   Nakanishi, Koji ^b   Berova, Nina ^b   Rosini, Carlo ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

^b Och Spine at New York Presbyterian Hospitals   (United States)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

Ab initio calculation; Absolute configuration; Circular dichroism; Indoline alkaloids; Optical rotation

Indexed keywords

1,2,3,3A,8,8A HEXAHYDRO 1,3A DIMETHYLPYRROLO[2,3 B]INDOLE; CHIMONANTHINE; INDOLE ALKALOID; MONOMER; NATURAL PRODUCT; OLIGOMER; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ARTICLE; CALCULATION; CIRCULAR DICHROISM; OPTICAL ROTATION; PRIORITY JOURNAL; RELIABILITY; SIMULATION; SPECTRAL SENSITIVITY; SYNTHESIS; THEORETICAL MODEL;

ALUMINUM; CHEMISTRY, ANALYTICAL; CIRCULAR DICHROISM; CYCLOHEXANES; ELECTRONICS; HYDROGEN; INDOLE ALKALOIDS; INDOLES; LITHIUM; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MONTE CARLO METHOD; SOFTWARE; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 34250192150     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20395     Document Type: Article

References (74)

1. Hino T, Nakagawa M. Chemistry and reactions of cyclic tautomers of tryptamines and tryptophans. In: Brossi A, editor. The alkaloids, Vol. 34. San Diego, CA: Academic Press; 1988. p 1-75.
2. Wrobel JT. Sulfur-containing alkaloids. In: Brossi A, editor. The alkaloids, Vol. 26. New York: Academic Press; 1985. p 53-87.
3. Anthoni U, Christophersen C, Nielsen PH. Naturally occurring cyclotryptophans and cyclotryptamines. In: Pelletier SW, editor. The alkaloids: chemical and biological perspectives, Vol. 14. New York: Wiley; 1999. p 163-236.
4. Hodson HF, Robinson B, Smith GF. Chimonanthine, a new calycanthaceous alkaloid. Proc Chem Soc Lond 1961;465-466.
5. Adjibade Y, Weniger B, Quirion JC, Kuballa B, Cabalion P, Anton R. Dimeric alkaloids from Psychotria forsteriana. Phytochemistry 1991;31:317-319.
6. Tokuyama T, Daly JW. Steroidal alkaloids (batrachotoxins and 4β-hydroxybatrachotoxins), indole alkaloids (calycanthine and chimonanthine) and a piperidinyldipyridine alkaloid (noranabasamine) in skin extracts from the Colombian poison-dart frog Phyllobates terribilis (Dendrobatidae). Tetrahedron 1983;39:41-47.
7. Verotta L, Pilati T, Tatò M, Elisabetsky E, Amador TA, Nunes DS. Pyrrolidinoindoline alkaloids from Psychotria colorata. J Nat Prod 1998;61:392-396.
8. Overman LE, Paone DV, Stearns BA. Direct stereo- and enantiocontrolled synthesis of vicinal stereogenic quaternary carbon centers. Total syntheses of meso- and (-)-chimonanthine and (+)-calycanthine. J Am Chem Soc 1999;121:7702-7703.
9. Overman LE, Larrow JF, Stearns BA, Vance JM, Enantioselective construction of vicinal stereogenic quaternary centers by dialkylation: Practical total syntheses of (+)- and meso-chimonanthine. Angew Chem Int Ed Engl 2000,39,213-215.
10. Koslowski A, Sreerama N, Woody RW. Theoretical approach to electronic optical activity. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism: principles and applications, 2nd ed. New York: Wiley; 2000. p 55-95.
11. Autschbach J, Ziegler T. Calculating molecular electric and magnetic properties from time-dependent density functional response theory. J Chem Phys 2002;116:891-896.
12. Frisch MJ, Trucks GW, Schlegel HB, et al. Gaussian03. Gaussian Inc., Pittsburgh, PA.
13. 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.
14. Autschbach J, Ziegler T, van Gisbergen SJA, Baerends EJ. Chiroptical properties from time-dependent density functional theory. I. Circular dichroism spectra of organic molecules. J Chem Phys 2002;116:6930-6940.
15. Pecul M, Ruud K, Helgaker T. Density functional theory calculation of electronic circular dichroism using London orbitals. Chem Phys Lett 2004;388:110-119.
16. Stephens PJ, McCann DM, Devlin FJ, Cheeseman JR, Frisch MJ. Determination of the absolute configuration of [32](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.
17. Neugebauer J, Baerends EJ, Nooijen M, Autschbach J. Importance of vibronic effects on the circular dichroism spectrum of dimethyloxirane. J Chem Phys 2005;122:234305/1-234305/7.
18. Pecul M, Marchesan D, Ruud K, Coriani S. Polarizable continuum model study of solvent effects on electronic circular dichroism parameters. J Chem Phys 2005;122:024106/1-024106/9.
19. Giorgio E, Tanaka K, Ding W, Krishnamurthy G, Pitts K, Elleslad GA, Rosini C, Berova N. Theoretical simulation of the electronic circular dichroism spectrum of calicheamicin. Bioorg Med Chem 2005;13:5072-5079.
20. Polavarapu PL. Optical rotation: Recent advances in determining the absolute configuration. Chirality 2002;14:768-781.
21. Polavarapu PL. The absolute configuration of bromochlorofluoromethane. Angew Chem Int Ed Engl 2002;41:4544-4546.
22. Polavarapu PL, Petrovic A, Wang F. Intrinsic rotation and molecular structure. Chirality 2003;15 (Suppl):S143-S149.
23. Petrovic AG, He J, Polavarapu PL, Xiao LS, Armstrong DW. Absolute configuration and predominant conformations of 1,1-dimethyl-2-phenylethyl phenyl sulfoxide. Org Biomol Chem 2005;3:1977-1981.
24. Petrovic AG, Polavarapu PL, Drabowicz J, Zhang Y, McConnell OJ, Duddeck H. Absolute configuration of C2-symmetric spiroselenurane: 3,3,3′, 3′-tetramethyl-1,1′-spirobi[3H,2.1]benzoxaselenole. Chem Eur J 2005;11:4257-4262.
25. Polavarapu PL, Kramers-Kronig transformation for optical rotatory dispersion studies. J Phys Chem A 2005;109:7013-7023.
26. Zuber G, Goldsmith MR, Hopkins TD, Beratan DN, Wipf P. Systematic assignment of the configuration of flexible natural products by spectroscopic and computational methods: the bistramide C analysis. Org Lett 2005;7:5269-5272.
27. Zuber G, Goldsmith MR, Beratan DN, Wipf P. Assignment of the absolute configuration of [n]-ladderanes by TD-DFT optical rotation calculations. Chirality 2005;17:507-510.
28. Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ, Hartree-Fock and density functional theory ab initio calculation of optical rotation using GIAOs: basis set dependence. J Phys Chem A 2000;104:1039-1046.
29. Stephens PJ, Devlin FJ, Cheeseman JR, Frisch MJ, Mennucci B, Tomasi J. Prediction of optical rotation using density functional theory: 6,8-dioxabicyclo[3.2.1]octanes. Tetrahedron: Asymmetry 2000;11:2443-2448.
30. Stephens PJ, Devlin FJ, Cheeseman JR, Frisch MJ. Calculation of optical rotation using density functional theory. J Phys Chem A 2001;105:5356-5371.
31. Stephens PJ, Devlin FJ, Cheeseman JR, Frisch MJ. 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.
32. Mennucci B, Tomasi J, Cammi R, Cheeseman JR, Frisch MJ, Devlin FJ, Gabriel S, Stephens PJ. Polarizable continuum model (PCM) calculations of solvent effects on optical rotations of chiral molecules. J Phys Chem A 2002;106:6102-6113.
33. Stephens PJ, Devlin FJ, Cheeseman JR, Frisch MJ, Rosini C. Determination of absolute configuration using optical rotation calculated using density functional theory. Org Lett 2002;4:4595-4598.
34. Stephens PJ, Devlin FJ, Cheeseman JR, Frisch MJ, Bortolini O, Besse P. Determination of absolute configuration using ab initio calculation of optical rotation. Chirality 2003;15 (Suppl):S57-S64.
35. Stephens PJ, McCann DM, Butkus E, Stoncius S, Cheeseman JR, Frisch MJ. 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.
36. Stephens PJ, McCann DM, Devlin FJ, Cheeseman JR, Frisch MJ. Determination of the absolute configuration of (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.
37. McCann DM, Stephens PJ, Cheeseman JR. Determination of absolute configuration using density functional theory calculation of optical rotation: Chiral alkanes. J Org Chem 2004;69:8709-8717.
38. Stephens PJ, McCann DM, Cheeseman JR, Frisch MJ. Determination of absolute configurations of chiral molecules using ab initio time-dependent density functional theory calculations of optical rotation: how reliable are absolute configurations obtained for molecules with small rotations? Chirality 2005;17 (Suppl):S52-S64.
39. McCann DM, Stephens PJ. 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.
40. Grimme S. Calculation of frequency dependent optical rotation using density functional response theory. Chem Phys Lett 2001;339:380-388.
41. Grimme S, Furche F, Ahlrichs R. An improved method for density functional calculations of the frequency-dependent optical rotation. Chem Phys Lett 2002;361:321-328.
42. Grimme S, Bahlmann A, Haufe G. Ab initio calculations for the optical rotations of conformationally flexible molecules: a case study on six-, seven-, and eight-membered fluorinated cycloalkanol esters. Chirality 2002;14:793-797.
43. De Meijere A, Khlebnikov A, Kozhushkov S, Kostikov RR, Schreiner PR, Wittkopp A, Rinderspacher C, Menzel H, Yufit DS, Howard JAK. The first enantiomerically pure [n]triangulanes and analogues: s-[n]helicenes with remarkable features. Chem Eur J 2002;8:828-842.
44. Crawford TD, Owens LS, Tain MC, Schreiner PR, Koch H. Ab initio calculation of optical rotation in (P)-(+)-[4]triangulane. J Am Chem Soc 2005;127:1368-1369.
45. Rinderspacher BC, Schreiner PR. Structure-property relationships of prototypical chiral compounds: case studies. J Phys Chem A 2004;108:2867-2870.
46. Tam MC, Russ NJ, Crawford TD. Coupled cluster calculations of optical rotatory dispersion of (S)-methyloxirane. J Chem Phys 2004;121:3550-3557.
47. Crawford TD. Ab initio calculation of molecular chiroptical properties. Theor Chem Acc 2006;115:227-245.
48. Autschbach J, Patchkovskii S, Ziegler T, van Gisbergen SJA, Baerends EJ. Chiroptical properties from time-dependent density functional theory. II. Optical rotations of small-to-medium sized organic molecules. J Chem Phys 2002;117:581-592.
49. Krykunov M, Autschbach J. Calculation of optical rotation with time-periodic magnetic-field-dependent basis functions in approximate time-dependent density-functional theory. J Chem Phys 2005;123:114103/1-114103/ 10.
50. Mort BC, Autschbach J. Magnitude of zero-point vibrational corrections to optical rotation in rigid organic molecules: a time-dependent density functional study. J Phys Chem A 2005;109:8617-8623.
51. Autschbach J, Jensen L, Schatz GC, Electra Tse YC, Krykunov M. Time-dependent density functional calculations of optical rotatory dispersion including resonance wavelengths as a potentially useful tool for determining absolute configurations of chiral molecules. J Phys Chem A 2006;110:2461-2473.
52. Ruud K, Taylor PR, Astrand PO. Zero-point vibrational effects on optical rotation. Chem Phys Lett 2001;337:217-223.
53. Ruud K, Helgaker T. Optical rotation studied by density-functional and coupled-cluster methods. Chem Phys Lett 2002;352:533-539.
54. Ruud K, Astrand PO, Taylor PR. Vibrational effects on molecular properties in large molecules. J Comp Methods Sci Eng 2003;3:7-39.
55. Ruud K, Stephens PJ, Devlin FJ, Taylor PR, Cheeseman JR, Frisch MJ. Coupled-cluster calculations of optical rotation. Chem Phys Lett 2003;373:606-614.
56. Pecul M, Ruud K, Rizzo A, Helgaker T. Conformational effects on the optical rotation of alanine and proline. J Phys Chem A 2004;108:4269-4276.
57. Norman P, Ruud K, Helgaker T. Density-functional theory calculations of optical rotatory dispersion in the nonresonant and resonant frequency regions. J Chem Phys 2004;120:5027-5035.
58. Ruud K, Zanasi R. The importance of molecular vibrations: the sign change of the optical rotation of methyloxirane. Angew Chem Int Ed Engl 2005;44:3594-3596.
59. Marchesan D, Coriani S, Forzato C, Nitti P, Pitacco G, Ruud K. Optical rotation calculation of a highly flexible molecule: the case of paraconic acid. J Phys Chem A 2005;109:1449-1453.
60. Giorgio E, Viglione RG, Rosini C. Assignment of the absolute configuration of large molecules by ab initio calculation of the rotatory power within a small basis set scheme: the case of some biologically active natural products. Tetrahedron: Asymmetry 2004;15:1979-1986.
61. Giorgio E, Rosini C, Viglione RG, Zanasi R. Calculation of the gas phase specific rotation of (S)-propylene oxide at 355 nm. Chem Phys Lett 2003;376:452-456.
62. Giorgio E, Viglione RG, Zanasi R, Rosini C. Ab initio calculation of optical rotatory dispersion (ORD) curves: a simple and reliable approach to the assignment of the molecular absolute configuration. J Am Chem Soc 2004;126:12968-12976.
63. Vogensen SB, Greenwood JR, Varming AR, Brehm L, Pickering DS, Nielsen B, Liljefors T, Clausen RP, Johansen TN, Krogsgaard-Larsen P. A stereochemical anomaly: The cyclized (R)-AMPA analogue (R)-3-hydroxy-4,5,6,7- tetrahydroisoxazolo[5,4-c[pyridine-5-carboxylic acid [(R)-5-HPCA] resembles (S)-AMPA at glutamate receptors. Org Biomol Chem 2004;2:206-213.
64. Giorgio E, Maddau L, Spanu E, Evidente A, Rosini C. Assignment of the absolute configuration of (+)-diplopyrone, the main phytotoxin produced by Diplodia mutila, the pathogen of the cork oak decline, by a nonempirical analysis of its chiroptical properties. J Org Chem 2005;70:7-13.
65. Giorgio E, Parrinello N, Caccamese S, Rosini C. Non-empirical assignment of the absolute configuration of (-)-naringenin, by coupling the exciton analysis of the circular dichroism spectrum and the ab initio calculation of the optical rotatory power. Org Biomol Chem 2004;2:3602-3607.
66. Giorgio E, Roje M, Tanaka K, Hamersak Z, Sunjic 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.
67. Giorgio E, Minichino C, Viglione RG, Zanasi R, Rosini C. Assignment of the molecular absolute configuration through the ab initio Hartree-Fock calculation of the optical rotation: can the circular dichroism data help in reducing basis set requirements? J Org Chem 2003;68:5186-5192.
68. Mason SF, Vane GW. The circular dichroism and absorption spectra of alkaloids containing the aniline chromophore. The absolute configuration of calycanthine. J Chem Soc B 1966;370-374.
69. SPARTAN '02. Wavefunction Inc., Irvine, CA; 2002. http://www.wavefun.com.
70. Kawahara M, Nishida A, Nakagawa M. An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization. Org Lett 2000;2:675-678.
71. Lebsack AD, Link JT, Overman LE, Stearns BA. Enantioselective total synthesis of quadrigemine C and psycholeine. J Am Chem Soc 2002;124:9008-9009.
72. Tsuji R, Nakagawa M, Nishida A. An efficient synthetic approach to optically active β-carboline derivatives via Pictet-Spengler reaction promoted by trimethylchlorosilane. Tetrahedron: Asymmetry 2003;14:177-180.
73. Verotta L, Orsini F, Sbacchi M, Scheildler MA, Amador TA, Elisabetsky E. Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-type alkaloids. Bioorg Med Chem 2002;10:2133-2142.
74. Parish CA, Dong JG, Bornmann WG, Chang J, Nakanishi K, Berova N. Circular dichroism studies of bisindole Vinca alkaloids. Tetrahedron 1998;54:15739-15758.