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Pure Appl. Chem., 1993, Vol. 65, No. 6, pp. 1329-1336

http://dx.doi.org/10.1351/pac199365061329

Superacidic cyclization of terpenoids

P. F. Vlad

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  • Li Zhilong, Lah Myoung Soo, Koo Sangho, Jung Heejung, Park Mira: Manganese(III)-Promoted Tandem Oxidation and Cyclization of β-Keto Ester Derivatives of Terpenoids. Synth Catal 2011, 353, 1913. <http://dx.doi.org/10.1002/adsc.201100215>
  • Godeau Julien, Olivero Sandra, Antoniotti Sylvain, Duñach Elisabet: Biomimetic Cationic Polyannulation Reaction Catalyzed by Bi(OTf)3: Cyclization of 1,6-Dienes, 1,6,10-Trienes, and Aryl Polyenes. Org Lett 2011, 13, 3320. <http://dx.doi.org/10.1021/ol201028f>
  • VLAD P. F.: ChemInform Abstract: Superacidic Cyclization of Terpenoids. ChemInform 2010, 24, no. <http://dx.doi.org/10.1002/chin.199336317>
  • Raptis Christos, Lykakis Ioannis N., Tsangarakis Constantinos, Stratakis Manolis: Acid-Catalyzed Cyclization of Terpenes Under Homogeneous and Heterogeneous Conditions as Probed Through Stereoisotopic Studies: A Concerted Process with Competing Preorganized Chair and Boat Transition States. Chem Eur J 2009, 15, 11918. <http://dx.doi.org/10.1002/chem.200901563>
  • Tsangarakis Constantinos, Raptis Christos, Arkoudis Elias, Stratakis Manolis: Zeolite NaY‐Promoted Monocyclization of Epoxy Polyene Terpenes: A Unique Route for the Direct Synthesis of Incompletely Cyclized Naturally Occurring Terpenols. Adv Synth Catal 2008, 350, 1587. <http://dx.doi.org/10.1002/adsc.200800180>
  • Grinco Marina, Kulciţki Veaceslav, Ungur Nicon, Jankowski Wieslaw, Chojnacki Tadeusz, Vlad Pavel F.: Superacid-Catalyzed Cyclization of Methyl (6Z)-Geranylfarnesoates. HCA 2007, 90, 1223. <http://dx.doi.org/10.1002/hlca.200790122>
  • Kulcitki V., Grin’ko M., Barba A., Ungur N., Vlad P. F.: Superacid cyclization of (2E,6E,10E,14E)-8-phenylsulfonylgeranylfarnesol tetrahydropyranyl ether. Chem Nat Compd 2007, 43, 268. <http://dx.doi.org/10.1007/s10600-007-0102-5>
  • Yu Wei, Bian Fengling, Gao Yuan, Yang Li, Liu Zhong-Li: Y-Zeolite-Catalyzed Cyclizations of Terpenols. Adv Synth Catal 2006, 348, 59. <http://dx.doi.org/10.1002/adsc.200505146>
  • Tsangarakis Constantinos, Stratakis Manolis: Stereoselective Disposition of the Geminal Dimethyl Group in the Cyclization of Geranyl Acetate under Zeolite Confinement Conditions. Eur J Org Chem 2006, 2006, 4435. <http://dx.doi.org/10.1002/ejoc.200600367>
  • Grin’ko M., Kul’chitskii V., Ungur N., Vlad P. F.: Superacid cyclization of certain aliphatic sesquiterpene derivatives in ionic liquids. Chem Nat Compd 2006, 42, 439. <http://dx.doi.org/10.1007/s10600-006-0175-6>
  • Tsangarakis Constantinos, Stratakis Manolis: Biomimetic Cyclization of Small Terpenoids Promoted by Zeolite NaY: Tandem Formation of α-Ambrinol from Geranyl Acetone. Adv Synth Catal 2005, 347, 1280. <http://dx.doi.org/10.1002/adsc.200505059>
  • Ungur Nicon, Kulciţki Veaceslav, Gavagnin Margherita, Castelluccio Francesco, Vlad Pavel F, Cimino Guido: Studies towards the synthesis of cheilanthane sesterterpenoids: superacidic cyclisation of methyl 13Z,17Z- and 13Z,17E-bicyclogeranylfarnesoates. Tetrahedron 2002, 58, 10159. <http://dx.doi.org/10.1016/S0040-4020(02)01399-6>
  • Franck-Neumann Michel, Geoffroy Philippe, Hanss David: Highly stereoselective biomimetic polyene cyclizations using chiral pentadienol tricarbonyliron complexes. Tetrahetron Lett 2002, 43, 2277. <http://dx.doi.org/10.1016/S0040-4039(02)00190-9>
  • Zhou Sheng-Ze, Sey Mario, De Clercq Pierre J., Milanesio Marco, Viterbo Davide: A Model for the Nonenzymatic BCD Cyclization of Squalene. Angew Chem 2000, 112, 2983. <http://dx.doi.org/10.1002/1521-3757(20000818)112:16<2983::AID-ANGE2983>3.0.CO;2-0>
  • Zhou Sheng-Ze, Sey Mario, De Clercq Pierre J., Milanesio Marco, Viterbo Davide: A Model for the Nonenzymatic BCD Cyclization of Squalene. Angew Chem 2000, 39, 2861. <http://dx.doi.org/10.1002/1521-3773(20000818)39:16<2861::AID-ANIE2861>3.0.CO;2-W>
  • Kulciţki V., Ungur N., Deleanu C., Vlaa P. F.: Superacidic cyclization of ω-hydroxygeraniol diacetate and ω-hydroxygeraniol benzyl ether acetate. Russ Chem Bull 1999, 48, 136. <http://dx.doi.org/10.1007/BF02494415>
  • Kulciţki Veaceslav, Ungur Nicon, Vlad Pavel F.: Superacidic low temperature cyclization of terpenylphenylsulfones. Tetrahedron 1998, 54, 11925. <http://dx.doi.org/10.1016/S0040-4020(98)83049-4>
  • Grayson David H.: Monoterpenoids. Nat Prod Rep 1997, 14, 477. <http://dx.doi.org/10.1039/np9971400477>
  • Lawrence Christopher, Bell Ian M., Abell Chris, Leeper Finian J.: Approaches to Antibody-Catalyzed Cationic Cyclizations: Chemical Studies of Leaving Groups and Cyclization Modes. Isr. J. Chem. 1996, 36, 161. <http://dx.doi.org/10.1002/ijch.199600022>
  • Schaeffer Philippe, Poinsot Jacques, Hauke Véréna, Adam Pierre, Wehrung Patrick, Trendel Jean-Michel, Albrecht Pierre, Dessort Daniel, Connan Jacques: Neue optisch aktive Kohlenwasserstoffe in Sedimenten: Hinweise auf eine weitgehende biologische Cyclisierung höherer regulärer Polyprenole. Angew Chem 1994, 106, 1235. <http://dx.doi.org/10.1002/ange.19941061117>
  • Schaeffer Philippe, Poinsot Jacques, Hauke Véréna, Adam Pierre, Wehrung Patrick, Trendel Jean-Michel, Albrecht Pierre, Dessort Daniel, Connan Jacques: Novel Optically Active Hydrocarbons in Sediments: Evidence for an Extensive Biological Cyclization of Higher Regular Polyprenols. Angew Chem Int Ed Engl 1994, 33, 1166. <http://dx.doi.org/10.1002/anie.199411661>
  • Ourisson Guy, Nakatani Yoichi: The terpenoid theory of the origin of cellular life: the evolution of terpenoids to cholesterol. CHEM BIOL 1994, 1, 11. <http://dx.doi.org/10.1016/1074-5521(94)90036-1>
  • Jordine Guido, Bick Stefan, Möller Uwe, Welzel Peter, Daucher Birgit, Maas Gerhard: Studies on forskolin ring C forming reactions. Tetrahedron 1994, 50, 139. <http://dx.doi.org/10.1016/S0040-4020(01)80741-9>