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Collect. Czech. Chem. Commun. 2003, 68, 202-210
https://doi.org/10.1135/cccc20030202

On the Concerted Ring Opening of Protonated Squalene Oxide and A-Ring Formation in the Biosynthesis of Lanosterol

B. Andes Hess, Jr.

Department of Chemistry, Vanderbilt University, Nashville, TN 37235, U.S.A.

Crossref Cited-by Linking

  • Diao Hongjuan, Chen Nanhao, Wang Kai, Zhang Fan, Wang Yong-Heng, Wu Ruibo: Biosynthetic Mechanism of Lanosterol: A Completed Story. ACS Catal. 2020, 10, 2157. <https://doi.org/10.1021/acscatal.9b05221>
  • Hess B. Andes, Smentek Lidia: The Concerted Nature of the Cyclization of Squalene Oxide to the Protosterol Cation. Angewandte Chemie 2013, 125, 11235. <https://doi.org/10.1002/ange.201302886>
  • Hess B. Andes, Smentek Lidia: The Concerted Nature of the Cyclization of Squalene Oxide to the Protosterol Cation. Angew Chem Int Ed 2013, 52, 11029. <https://doi.org/10.1002/anie.201302886>
  • 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>
  • Coxon James M., Townsend Michael A.E.: Five- and six-membered ring formation from the intramolecular reaction of a protonated oxirane and alkene. Tetrahedron 2008, 64, 9654. <https://doi.org/10.1016/j.tet.2008.06.109>
  • Coxon James M., Townsend Michael A.E.: Computational study on the ring-opening reaction of protonated oxirane and methylpropene. Tetrahedron 2007, 63, 5665. <https://doi.org/10.1016/j.tet.2007.03.168>
  • Nowroozi-Isfahani Taraneh, Musaev Djamaladdin G., Morokuma Keiji, Gagné Michel R.: Density Functional Study of Platinum(II)-Mediated Bicyclization of 1,6-Dienylphenols. Organometallics 2007, 26, 2540. <https://doi.org/10.1021/om060632f>
  • Matsuda Seiichi P. T., Wilson William K., Xiong Quanbo: Mechanistic insights into triterpene synthesis from quantum mechanical calculations. Detection of systematic errors in B3LYP cyclization energies. Org. Biomol. Chem. 2006, 4, 530. <https://doi.org/10.1039/b513599k>
  • Hess B. Andes: Formation of the B Ring in Steroids and Hopanoids from Squalene. Eur J Org Chem 2004, 2004, 2239. <https://doi.org/10.1002/ejoc.200300684>
  • Hess B. Andes, Smentek Lidia: Concerted Nature of AB Ring Formation in the Enzymatic Cyclization of Squalene to Hopenes. Org. Lett. 2004, 6, 1717. <https://doi.org/10.1021/ol0496125>
  • Andes Hess B., Smentek Lidia: Density functional study on formation of A and B rings in conversion of 2,3-oxidosqualene to lanosterol. Molecular Physics 2004, 102, 1201. <https://doi.org/10.1080/00268970410001728726>
  • Hess B. Andes: Formation of Ring A in the Biosynthesis of Hopanoids from Squalene. A Density Functional Study. Collect. Czech. Chem. Commun. 2004, 69, 261. <https://doi.org/10.1135/cccc20040261>