Caryolene-forming carbocation rearrangements

Scholarly Works

• Kumar, R. P.; Matos, J. O.; Black, B. Y.; Ellenburg, W. H.; Chen, J.; Patterson, M.; Gehtman, J. A.; Theobald, D. L.; Krauss, I. J.; Oprian, D. D. Crystal Structure of Caryolan-1-ol Synthase, a Sesquiterpene Synthase Catalyzing an Initial Anti-Markovnikov Cyclization Reaction. Biochemistry 2024, 63, 2904–2915. doi:10.1021/acs.biochem.4c00547
• Nakano, M.; Gemma, R.; Sato, H. Unraveling the role of prenyl side-chain interactions in stabilizing the secondary carbocation in the biosynthesis of variexenol B. Beilstein journal of organic chemistry 2023, 19, 1503–1510. doi:10.3762/bjoc.19.107
• Paknikar, S. K.; Fondekar, K. P. Recent Developments in Selected Sesquiterpenes: Molecular Rearrangements, Biosynthesis, and Structural Relationship among Congeners. Terpenes and Terpenoids; IntechOpen, 2018. doi:10.5772/intechopen.74998
• Pedrón, M.; Delso, J. I.; Tejero, T.; Merino, P. Concerted Albeit Not Pericyclic Cycloadditions: Understanding the Mechanism of the (4+3) Cycloaddition between Nitrones and 1,2-Diaza-1,3-dienes. European Journal of Organic Chemistry 2018, 2019, 391–400. doi:10.1002/ejoc.201800663
• Rablen, P. R. Acid-Catalyzed Conversion Of Caryolan-1-ol To Isoclovene: A Computational Investigation Of The Multi-Step Carbocation Rearrangement. Tetrahedron 2018, 74, 3781–3786. doi:10.1016/j.tet.2018.04.031
• Newton, C. G.; Tran, D. N.; Wodrich, M. D.; Cramer, N. One-Step Multigram-Scale Biomimetic Synthesis of Psiguadial B. Angewandte Chemie (International ed. in English) 2017, 56, 13776–13780. doi:10.1002/anie.201708333
• Newton, C. G.; Tran, D. N.; Wodrich, M. D.; Cramer, N. One‐Step Multigram‐Scale Biomimetic Synthesis of Psiguadial B. Angewandte Chemie 2017, 129, 13964–13968. doi:10.1002/ange.201708333
• Chiacchio, M. A.; Legnani, L.; Caramella, P.; Tejero, T.; Merino, P. Pivotal Neighboring-Group Participation in Substitution versus Elimination Reactions – Computational Evidence for Ion Pairs in the Thionation of Alcohols with Lawesson's Reagent. European Journal of Organic Chemistry 2017, 2017, 1952–1960. doi:10.1002/ejoc.201700127
• Le Bideau, F.; Kousara, M.; Chen, L.; Wei, L.; Dumas, F. Tricyclic Sesquiterpenes from Marine Origin. Chemical reviews 2017, 117, 6110–6159. doi:10.1021/acs.chemrev.6b00502
• Nguyen, Q. N. N.; Tantillo, D. J. Using quantum chemical computations of NMR chemical shifts to assign relative configurations of terpenes from an engineered Streptomyces host. The Journal of antibiotics 2016, 69, 534–540. doi:10.1038/ja.2016.51
• Ortega, D. E.; Nguyen, Q. N. N.; Tantillo, D. J.; Toro-Labbé, A. The catalytic effect of the NH3 base on the chemical events in the caryolene-forming carbocation cascade. Journal of computational chemistry 2016, 37, 1068–1081. doi:10.1002/jcc.24294
• Krenske, E. H.; Williams, C. M. Do Anti‐Bredt Natural Products Exist? Olefin Strain Energy as a Predictor of Isolability. Angewandte Chemie 2015, 127, 10754–10758. doi:10.1002/ange.201503822
• Krenske, E. H.; Williams, C. M. Do anti-Bredt natural products exist? Olefin strain energy as a predictor of isolability. Angewandte Chemie (International ed. in English) 2015, 54, 10608–10612. doi:10.1002/anie.201503822
• White, A. M.; Pierens, G. K.; Skinner-Adams, T. S.; Andrews, K. T.; Bernhardt, P. V.; Krenske, E. H.; Mollo, E.; Garson, M. J. Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata. Journal of natural products 2015, 78, 1422–1427. doi:10.1021/acs.jnatprod.5b00354
• Hare, S. R.; Orman, M.; Dewan, F.; Dalchand, E.; Buzard, C.; Ahmed, S.; Tolentino, J. C.; Sethi, U.; Terlizzi, K.; Houferak, C.; Stein, A. M.; Stedronsky, A.; Thamattoor, D. M.; Tantillo, D. J.; Merrer, D. C. Experimental and computational mechanistic investigation of chlorocarbene additions to bridgehead carbene-anti-Bredt systems: noradamantylcarbene-adamantene and adamantylcarbene-homoadamantene. The Journal of organic chemistry 2015, 80, 5049–5065. doi:10.1021/acs.joc.5b00456
• Hamlin, T. A.; Hamann, C. S.; Tantillo, D. J. Delocalization of charge and electron density in the humulyl cation—implications for terpene biosynthesis. The Journal of organic chemistry 2015, 80, 4046–4053. doi:10.1021/acs.joc.5b00381
• Hong, Y. J.; Tantillo, D. J. Feasibility of intramolecular proton transfers in terpene biosynthesis--guiding principles. Journal of the American Chemical Society 2015, 137, 4134–4140. doi:10.1021/ja512685x
• Mak, J. Y. W.; Pouwer, R. H.; Williams, C. M. Naturstoffe mit Anti‐Bredt‐ und Brückenkopf‐Doppelbindung. Angewandte Chemie 2014, 126, 13882–13906. doi:10.1002/ange.201400932
• Mak, J. Y. W.; Pouwer, R. H.; Williams, C. M. Natural Products with Anti-Bredt and Bridgehead Double Bonds. Angewandte Chemie (International ed. in English) 2014, 53, 13664–13688. doi:10.1002/anie.201400932
• Hong, Y. J.; Tantillo, D. J. How cyclobutanes are assembled in nature – insights from quantum chemistry. Chemical Society reviews 2014, 43, 5042–5050. doi:10.1039/c3cs60452g

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