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Collect. Czech. Chem. Commun. 2008, 73, 786-794
https://doi.org/10.1135/cccc20080786

The Concerted Nature of the Enzymatic Cyclization of Rings A-D of Squalene to Hopene

B. Andes Hess, Jr.a,* and Lidia Smenteka,b

a Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, U.S.A.
b Institute of Physics, N. Copernicus University, 87-100 Toruń, Poland

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  • Hong Young J., Tantillo Dean J.: A Maze of Dyotropic Rearrangements and Triple Shifts: Carbocation Rearrangements Connecting Stemarene, Stemodene, Betaerdene, Aphidicolene, and Scopadulanol. J. Org. Chem. 2018, 83, 3780. <https://doi.org/10.1021/acs.joc.8b00138>
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  • Hong Young J., Giner José-Luis, Tantillo Dean J.: Triple Shifts and Thioether Assistance in Rearrangements Associated with an Unusual Biomethylation of the Sterol Side Chain. J. Org. Chem. 2013, 78, 935. <https://doi.org/10.1021/jo3024208>
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  • Hess B. Andes, Smentek Lidia, Noel Joseph P., O’Maille Paul E.: Physical Constraints on Sesquiterpene Diversity Arising from Cyclization of the Eudesm-5-yl Carbocation. J. Am. Chem. Soc. 2011, 133, 12632. <https://doi.org/10.1021/ja203342p>
  • Tantillo Dean J.: Biosynthesis via carbocations: Theoretical studies on terpene formation. Nat Prod Rep 2011, 28, 1035. <https://doi.org/10.1039/c1np00006c>
  • Smentek Lidia, Hess B. Andes: Compelling Computational Evidence for the Concerted Cyclization of the ABC Rings of Hopene from Protonated Squalene. J. Am. Chem. Soc. 2010, 132, 17111. <https://doi.org/10.1021/ja1039133>
  • Hong Young J., Tantillo Dean J.: Formation of Beyerene, Kaurene, Trachylobane, and Atiserene Diterpenes by Rearrangements That Avoid Secondary Carbocations. J. Am. Chem. Soc. 2010, 132, 5375. <https://doi.org/10.1021/ja9084786>
  • Tantillo Dean J.: The carbocation continuum in terpene biosynthesis—where are the secondary cations?. Chem. Soc. Rev. 2010, 39, 2847. <https://doi.org/10.1039/b917107j>