Structural Reassignment of Obtusallenes V, VI, and VII by GIAO-Based Density Functional Prediction

This article is cited by 48 publications.

1. Erin D. Shepherd, Bryony S. Dyson, William E. Hak, Quynh Nhu N. Nguyen, Miseon Lee, Mi Jung Kim, Te-ik Sohn, Deukjoon Kim, Jonathan W. Burton, Robert S. Paton. Structure Determination of a Chloroenyne from Laurencia majuscula Using Computational Methods and Total Synthesis. The Journal of Organic Chemistry 2019, 84 (9) , 4971-4991. https://doi.org/10.1021/acs.joc.8b02975
2. Henry S. Rzepa, Sergey Arkhipenko, Emily Wan, Marco T. Sabatini, Valerija Karaluka, Andrew Whiting, Tom D. Sheppard. An Accessible Method for DFT Calculation of 11B NMR Shifts of Organoboron Compounds. The Journal of Organic Chemistry 2018, 83 (15) , 8020-8025. https://doi.org/10.1021/acs.joc.8b00859
3. Sylvain Sutour, Bruno Therrien, Stephan H. von Reuss, and Félix Tomi . Halogenated C15 Acetogenin Analogues of Obtusallene III from a Laurenciella sp. Collected in Corsica. Journal of Natural Products 2018, 81 (2) , 279-285. https://doi.org/10.1021/acs.jnatprod.7b00706
4. Andrei G. Kutateladze and Dmitry M. Kuznetsov . Triquinanes and Related Sesquiterpenes Revisited Computationally: Structure Corrections of Hirsutanols B and D, Hirsutenol E, Cucumin B, Antrodins C–E, Chondroterpenes A and H, Chondrosterins C and E, Dichrocephone A, and Pethybrene. The Journal of Organic Chemistry 2017, 82 (20) , 10795-10802. https://doi.org/10.1021/acs.joc.7b02018
5. Andrei G. Kutateladze and D. Sai Reddy . High-Throughput in Silico Structure Validation and Revision of Halogenated Natural Products Is Enabled by Parametric Corrections to DFT-Computed 13C NMR Chemical Shifts and Spin–Spin Coupling Constants. The Journal of Organic Chemistry 2017, 82 (7) , 3368-3381. https://doi.org/10.1021/acs.joc.7b00188
6. James Clarke, Karl J. Bonney, Muhammad Yaqoob, Savade Solanki, Henry S. Rzepa, Andrew J. P. White, David S. Millan, and D. Christopher Braddock . Epimeric Face-Selective Oxidations and Diastereodivergent Transannular Oxonium Ion Formation Fragmentations: Computational Modeling and Total Syntheses of 12-Epoxyobtusallene IV, 12-Epoxyobtusallene II, Obtusallene X, Marilzabicycloallene C, and Marilzabicycloallene D. The Journal of Organic Chemistry 2016, 81 (20) , 9539-9552. https://doi.org/10.1021/acs.joc.6b02008
7. Adrián Gutiérrez-Cepeda, José J. Fernández, Manuel Norte, Matías López-Rodríguez, Iván Brito, Christian D. Muller, and María L. Souto . Additional Insights into the Obtusallene Family: Components of Laurencia marilzae. Journal of Natural Products 2016, 79 (4) , 1184-1188. https://doi.org/10.1021/acs.jnatprod.5b01080
8. Keith G. Andrews and Alan C. Spivey . Improving the Accuracy of Computed 13C NMR Shift Predictions by Specific Environment Error Correction: Fragment Referencing. The Journal of Organic Chemistry 2013, 78 (22) , 11302-11317. https://doi.org/10.1021/jo401833b
9. Bin-Gui Wang, James B. Gloer, Nai-Yun Ji, and Jian-Chun Zhao . Halogenated Organic Molecules of Rhodomelaceae Origin: Chemistry and Biology. Chemical Reviews 2013, 113 (5) , 3632-3685. https://doi.org/10.1021/cr9002215
10. Susan G. Brown, Matthew J. Jansma, and Thomas R. Hoye . Case Study of Empirical and Computational Chemical Shift Analyses: Reassignment of the Relative Configuration of Phomopsichalasin to That of Diaporthichalasin. Journal of Natural Products 2012, 75 (7) , 1326-1331. https://doi.org/10.1021/np300248w
11. Ariel M. Sarotti and Silvina C. Pellegrinet . Application of the Multi-standard Methodology for Calculating 1H NMR Chemical Shifts. The Journal of Organic Chemistry 2012, 77 (14) , 6059-6065. https://doi.org/10.1021/jo3008447
12. Bryony S. Dyson, Jonathan W. Burton, Te-ik Sohn, Byungsook Kim, Hoon Bae, and Deukjoon Kim . Total Synthesis and Structure Confirmation of Elatenyne: Success of Computational Methods for NMR Prediction with Highly Flexible Diastereomers. Journal of the American Chemical Society 2012, 134 (28) , 11781-11790. https://doi.org/10.1021/ja304554e
13. Adrián Gutiérrez-Cepeda, José J. Fernández, Manuel Norte, and María L. Souto . New Bicyclotridecane C15 Nonterpenoid Bromoallenes from Laurencia marilzae. Organic Letters 2011, 13 (10) , 2690-2693. https://doi.org/10.1021/ol200792v
14. Giacomo Saielli, K. C. Nicolaou, Adrian Ortiz, Hongjun Zhang, and Alessandro Bagno . Addressing the Stereochemistry of Complex Organic Molecules by Density Functional Theory-NMR: Vannusal B in Retrospective. Journal of the American Chemical Society 2011, 133 (15) , 6072-6077. https://doi.org/10.1021/ja201108a
15. Steven G. Smith and Jonathan M. Goodman. Assigning Stereochemistry to Single Diastereoisomers by GIAO NMR Calculation: The DP4 Probability. Journal of the American Chemical Society 2010, 132 (37) , 12946-12959. https://doi.org/10.1021/ja105035r
16. Ariel M. Sarotti and Silvina C. Pellegrinet. A Multi-standard Approach for GIAO 13C NMR Calculations. The Journal of Organic Chemistry 2009, 74 (19) , 7254-7260. https://doi.org/10.1021/jo901234h
17. Steven G. Smith and Jonathan M. Goodman. Assigning the Stereochemistry of Pairs of Diastereoisomers Using GIAO NMR Shift Calculation. The Journal of Organic Chemistry 2009, 74 (12) , 4597-4607. https://doi.org/10.1021/jo900408d
18. José Alberto Mendoza-Espinoza, Fabian López-Vallejo, Mabel Fragoso-Serrano, Rogelio Pereda-Miranda and Carlos M. Cerda-García-Rojas. Structural Reassignment, Absolute Configuration, and Conformation of Hypurticin, a Highly Flexible Polyacyloxy-6-heptenyl-5,6-dihydro-2H-pyran-2-one. Journal of Natural Products 2009, 72 (4) , 700-708. https://doi.org/10.1021/np800447k
19. D. Christopher Braddock, David S. Millan, Yolanda Pérez-Fuertes, Rebecca H. Pouwer, Richard N. Sheppard, Savade Solanki and Andrew J. P. White. Bromonium Ion Induced Transannular Oxonium Ion Formation−Fragmentation in Model Obtusallene Systems and Structural Reassignment of Obtusallenes V−VII. The Journal of Organic Chemistry 2009, 74 (5) , 1835-1841. https://doi.org/10.1021/jo8026577
20. Daniel K. Nielsen, Laura L. Nielsen, Spencer B. Jones, Lawrence Toll, Matthew C. Asplund and Steven L. Castle. Synthesis of Isohasubanan Alkaloids via Enantioselective Ketone Allylation and Discovery of an Unexpected Rearrangement. The Journal of Organic Chemistry 2009, 74 (3) , 1187-1199. https://doi.org/10.1021/jo802370v
21. Jing Yang, Sheng-Xiong Huang and Qin-Shi Zhao . Structure Revision of Hassananes with Use of Quantum Mechanical 13C NMR Chemical Shifts and UV−Vis Absorption Spectra. The Journal of Physical Chemistry A 2008, 112 (47) , 12132-12139. https://doi.org/10.1021/jp8072415
22. Jim Downing, Peter Murray-Rust, Alan P. Tonge, Peter Morgan, Henry S. Rzepa, Fiona Cotterill, Nick Day and Matt J. Harvey . SPECTRa: The Deposition and Validation of Primary Chemistry Research Data in Digital Repositories. Journal of Chemical Information and Modeling 2008, 48 (8) , 1571-1581. https://doi.org/10.1021/ci7004737
23. Steven G. Smith, Robert S. Paton, Jonathan W. Burton and Jonathan M. Goodman. Stereostructure Assignment of Flexible Five-Membered Rings by GIAO 13C NMR Calculations: Prediction of the Stereochemistry of Elatenyne. The Journal of Organic Chemistry 2008, 73 (11) , 4053-4062. https://doi.org/10.1021/jo8003138
24. Fabio L. P. Costa, Ana C. F. de Albuquerque, Rodolfo G. Fiorot, Luciano M. Lião, Lucas H. Martorano, Gunar V. S. Mota, Alessandra L. Valverde, José W. M. Carneiro, Fernando M. dos Santos Junior. Structural characterisation of natural products by means of quantum chemical calculations of NMR parameters: new insights. Organic Chemistry Frontiers 2021, 8 (9) , 2019-2058. https://doi.org/10.1039/D1QO00034A
25. Zhiwei Zhang, Mada Triandala Sibero, Akiho Kai, Keisuke Fukaya, Daisuke Urabe, Yasuhiro Igarashi. TMKS8A, an antibacterial and cytotoxic chlorinated α-lapachone, from a sea slug-derived actinomycete of the genus Streptomyces. The Journal of Antibiotics 2021, 14 https://doi.org/10.1038/s41429-021-00415-4
26. Hau Sun Sam Chan, Amber L. Thompson, Kirsten E. Christensen, Jonathan W. Burton. Forwards and backwards – synthesis of Laurencia natural products using a biomimetic and retrobiomimetic strategy incorporating structural reassignment of laurefurenynes C–F. Chemical Science 2020, 6 https://doi.org/10.1039/D0SC04120C
27. Dominique Toledo, Francisco Brovelli, Jorge Soto-Delgado, Octavio Peña, Jean-Yves Pivan, Yanko Moreno. Influence of structural changes on photophysical properties of terpyridine derivates: Experimental studies and theoretical calculations. Journal of Molecular Structure 2018, 1153 , 282-291. https://doi.org/10.1016/j.molstruc.2017.10.011
28. Gabriela da Costa Resende, Elson Santiago Alvarenga. Structural elucidation of dioxa-cage compounds from tetrahydroisobenzofuran-1(3 H )-one: analysis of NMR data and GIAO chemical shifts calculations. Magnetic Resonance in Chemistry 2016, 54 (12) , 968-974. https://doi.org/10.1002/mrc.4483
29. Nicolas Grimblat, Ariel M. Sarotti. Computational Chemistry to the Rescue: Modern Toolboxes for the Assignment of Complex Molecules by GIAO NMR Calculations. Chemistry - A European Journal 2016, 22 (35) , 12246-12261. https://doi.org/10.1002/chem.201601150
30. Milena G. Teixeira, Elson S. Alvarenga. Characterization of novel isobenzofuranones by DFT calculations and 2D NMR analysis. Magnetic Resonance in Chemistry 2016, 54 (8) , 623-631. https://doi.org/10.1002/mrc.4411
31. Maria Harizani, Efstathia Ioannou, Vassilios Roussis. The Laurencia Paradox: An Endless Source of Chemodiversity. 2016,,, 91-252. https://doi.org/10.1007/978-3-319-33172-0_2
32. Girolamo Casella, Alessandro Bagno, Stanislav Komorovsky, Michal Repisky, Giacomo Saielli. Four-Component Relativistic DFT Calculations of 13 C Chemical Shifts of Halogenated Natural Substances. Chemistry - A European Journal 2015, 21 (51) , 18834-18840. https://doi.org/10.1002/chem.201502252
33. Alessandro Bagno, Giacomo Saielli. Addressing the stereochemistry of complex organic molecules by density functional theory-NMR. Wiley Interdisciplinary Reviews: Computational Molecular Science 2015, 5 (2) , 228-240. https://doi.org/10.1002/wcms.1214
34. Túlio J. Aímola, Dimas J. P. Lima, Luiz C. Dias, Cláudio F. Tormena, Marco A. B. Ferreira. 1 H chemical shift differences of Prelog–Djerassi lactone derivatives: DFT and NMR conformational studies. Organic & Biomolecular Chemistry 2015, 13 (7) , 2140-2145. https://doi.org/10.1039/C4OB02446J
35. Yang Li. Structural revision of glabramycins B and C, antibiotics from the fungus Neosartorya glabra by DFT calculations of NMR chemical shifts and coupling constants. RSC Advances 2015, 5 (46) , 36858-36864. https://doi.org/10.1039/C5RA01753J
36. Jean-Michel Kornprobst. Eubacteria - 2. 2014,,, 1-62. https://doi.org/10.1002/9783527335855.marprod008
37. Xianghua Zeng, Chengxia Miao, Shoufeng Wang, Chungu Xia, Wei Sun. Asymmetric 5-endo chloroetherification of homoallylic alcohols toward the synthesis of chiral β-chlorotetrahydrofurans. Chemical Communications 2013, 49 (24) , 2418. https://doi.org/10.1039/c2cc38436a
38. Dean J. Tantillo. Walking in the woods with quantum chemistry – applications of quantum chemical calculations in natural products research. Natural Product Reports 2013, 30 (8) , 1079. https://doi.org/10.1039/c3np70028c
39. Ariel M. Sarotti. Successful combination of computationally inexpensive GIAO 13C NMR calculations and artificial neural network pattern recognition: a new strategy for simple and rapid detection of structural misassignments. Organic & Biomolecular Chemistry 2013, 11 (29) , 4847. https://doi.org/10.1039/c3ob40843d
40. Lu Zhang, Shi-Qiong Wang, Xiao-Jun Li, An-Ling Zhang, Qiang Zhang, Jin-Ming Gao. New insight into the stereochemistry of botryosphaeridione from a Phoma endophyte. Journal of Molecular Structure 2012, 1016 , 72-75. https://doi.org/10.1016/j.molstruc.2012.02.041
41. Takashi L. Suyama, William H. Gerwick, Kerry L. McPhail. Survey of marine natural product structure revisions: A synergy of spectroscopy and chemical synthesis. Bioorganic & Medicinal Chemistry 2011, 19 (22) , 6675-6701. https://doi.org/10.1016/j.bmc.2011.06.011
42. Ryszard B. Nazarski, Beata Pasternak, Stanisław Leśniak. Three-component conformational equilibria of some flexible pyrrolidin-2-(thi)ones in solution by NMR data (δC, δH, and nJHH) and their DFT predictions: a confrontation of different approaches. Tetrahedron 2011, 67 (36) , 6901-6916. https://doi.org/10.1016/j.tet.2011.06.095
43. Aurelio San Martin, Juana Rovinosa, Alvaro Carrasco, Silvia Orejarena, Jorge Soto-Delgado, Renato Contreras, M. Cristina Chamy. Microbial Transformation of Marine Halogenated Sesquiterpenes. Natural Product Communications 2010, 5 (12) , 1934578X1000501. https://doi.org/10.1177/1934578X1000501203
44. Steven G. Smith, Julia A. Channon, Ian Paterson, Jonathan M. Goodman. The stereochemical assignment of acyclic polyols: a computational study of the NMR data of a library of stereopentad sequences from polyketide natural products. Tetrahedron 2010, 66 (33) , 6437-6444. https://doi.org/10.1016/j.tet.2010.06.022
45. Simone Di Micco, Maria Giovanna Chini, Raffaele Riccio, Giuseppe Bifulco. Quantum Mechanical Calculation of NMR Parameters in the Stereostructural Determination of Natural Products. European Journal of Organic Chemistry 2010, 2010 (8) , 1411-1434. https://doi.org/10.1002/ejoc.200901255
46. Marcelo A. Muñoz, Pedro Joseph-Nathan. DFT-GIAO 1 H and 13 C NMR prediction of chemical shifts for the configurational assignment of 6β-hydroxyhyoscyamine diastereoisomers. Magnetic Resonance in Chemistry 2009, 47 (7) , 578-584. https://doi.org/10.1002/mrc.2432
47. Carlos Areche, Aurelio San-Martín, Juana Rovirosa, Jorge Soto-Delgado, Renato Contreras. An unusual halogenated meroditerpenoid from Stypopodium flabelliforme: Studies by NMR spectroscopic and computational methods. Phytochemistry 2009, 70 (10) , 1315-1320. https://doi.org/10.1016/j.phytochem.2009.07.017
48. Charlotte S. M. Allan, Henry S. Rzepa. A computational investigation of the structure of polythiocyanogen. Dalton Trans. 2008, 14 (48) , 6925-6932. https://doi.org/10.1039/B810147G