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Pure Appl. Chem., 1989, Vol. 61, No. 3, pp. 539-542

http://dx.doi.org/10.1351/pac198961030539

Terpenoids from bark beetles, solitary bees and danaine butterflies

Wittko Francke, Jochen Bartels, Ernst Baader, Sabine Krohn, J. Tengo, S. Schulz and D. Schneider

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  • Sousa Gerimário F., Monteiro Hugo J., Resck Inês S., Gatto Claudia C., Ellena Javier, Sabino José R.: X-ray Crystal Structures of Intermediates of the Stereoselective (±)-Grandisol Synthesis Based on the Remote Alkylation Protocol. J Chem Crystallogr 2013, 43, 240. <http://dx.doi.org/10.1007/s10870-013-0411-4>
  • Pulido Francisco J., Barbero Asunción, García Carlos: Pd-catalyzed cross-coupling of allylsilane-vinylcopper species with aryl and vinyl halides: the first total synthesis of (−)-nomadone. Tetrahedron 2009, 65, 5535. <http://dx.doi.org/10.1016/j.tet.2009.01.118>
  • Gupta Pankaj, Sethi Vijay K., Taneja Subhash C., Shah Bhahwal A., Andotra Samar S., Koul Surrinder, Chimni Swapandeep S., Qazi Ghulam N.: Odoriferous Cyclic Ethersvia Co-Halogenation Reaction: Facile Preparation of Nerol Oxide,Florol®,Florol® Methyl Ether, andPityol® Methyl Ether. HCA 2007, 90, 196. <http://dx.doi.org/10.1002/hlca.200790016>
  • Monteiro Hugo J., Stefani Helio A.: A New Stereoselective Synthesis of (±)-Grandisol Based on the Remote Alkylation Protocol. Eur J Org Chem 2001, 2001, 2659. <http://dx.doi.org/10.1002/1099-0690(200107)2001:14<2659::AID-EJOC2659>3.0.CO;2-X>
  • Steinreiber Andreas, Edegger Klaus, Mayer Sandra F., Faber Kurt: Enantio- and diastereo-convergent synthesis of (2R,5R)- and (2R,5S)-Pityol through enzyme-triggered ring closure. Tet Asymm 2001, 12, 2067. <http://dx.doi.org/10.1016/S0957-4166(01)00370-6>
  • Hartung Jens, Schwarz Michaela, Svoboda Ingrid, Fuess Hartmut, Duarte Maria Teresa: A New Generation of Alkoxyl Radical Precursors – Preparation and Properties ofN-(Alkoxy)-4-arylthiazole-2(3H)-thiones. Eur J Org Chem 1999, 1999, 1275. <http://dx.doi.org/10.1002/(SICI)1099-0690(199906)1999:6<1275::AID-EJOC1275>3.0.CO;2-2>
  • Einhorn J., Guerrero A., Ducrot P.-H., Boyer F.-D., Gieselmann M., Roelofs W.: Sex pheromone of the oleander scale, Aspidiotus nerii: Structural characterization and absolute configuration of an unusual functionalized cyclobutane. Proceedings of the National Academy of Sciences 1998, 95, 9867. <http://dx.doi.org/10.1073/pnas.95.17.9867>
  • Schulz Stefan, Gross Jürgen, Hilker Monika: Origin of the defensive secretion of the leaf beetle Chrysomela lapponica. Tetrahedron 1997, 53, 9203. <http://dx.doi.org/10.1016/S0040-4020(97)00618-2>
  • Nishida R., Schulz S., Kim C. S., Fukami H., Kuwahara Y., Honda K., Hayashi N.: Male sex pheromone of a giant danaine butterfly,Idea leuconoe. J Chem Ecol 1996, 22, 949. <http://dx.doi.org/10.1007/BF02029947>
  • Alibés Ramón, Bourdelande José L., Font Josep, Parella Teodoro: Highly efficient and diastereoselective approaches to (+)- and (−)-grandisol. Tetrahedron 1996, 52, 1279. <http://dx.doi.org/10.1016/0040-4020(95)00958-2>
  • Schulz S., Nishida R.: The pheromone system of the male danaine butterfly, Idea leuconoe. biorg med chem 1996, 4, 341. <http://dx.doi.org/10.1016/0968-0896(96)00011-9>
  • Monteiro Hugo J., Zukerman-Schpector Julio: A new practical synthesis of (+)-grandisol from (+)-citronellol using an intramolecular carbenoid cyclization. Tetrahedron 1996, 52, 3879. <http://dx.doi.org/10.1016/S0040-4020(96)00175-5>
  • Confalonieri Giovanni, Marotta Emanuela, Rama Franco, Righi Paolo, Rosini Goffredo, Serra Rossella, Venturelli Francesca: Practical preparation of bicyclo[3.2.0]hept-3-en-6-ones and its utilisation in stereoselective total synthesis of grandisol and lineatin via a versatile intermediate. Tetrahedron 1994, 50, 3235. <http://dx.doi.org/10.1016/S0040-4020(01)81119-4>
  • Mischitz Martin, Hackinger Alexandra, Francesconi Iris, Faber Kurt: Enzyme-triggered opening of an epoxide: Chemoenzymatic synthesis of (2R,5R)- and (2S,5R)-pityol. Tetrahedron 1994, 50, 8661. <http://dx.doi.org/10.1016/S0040-4020(01)85340-0>
  • Mori Kenji, Aki Shinji, Kido Masaru: Pheromone synthesis, CXLVII. – Synthesis of (1R,3S,6R,9S,10S)-9,10-Epoxytetrahydroedulan, the Main Component of the Hairpencil Secretion of Male Danaid ButterflyEuploea klugii. Liebigs Ann Chem 1993, 1993, 83. <http://dx.doi.org/10.1002/jlac.199319930114>
  • Kohnle U., Densborn S., Kölsch P., Meyer H., Francke W.: E-7-methyl-1,6-dioxaspiro[4.5]decane in the chemical communication of European Scolytidae and Nitidulidae (Coleoptera). J Appl Entomol 1992, 114, 187. <http://dx.doi.org/10.1111/j.1439-0418.1992.tb01113.x>
  • Hoffmann Norbert, Scharf Hans-Dieter: Efficient and diastereoselective synthesis of (+)- and (−)-grandisol and 2-[(1R,2S)-2-isopropenylcyclobutyl]ethanol (demethylgrandisol) in high purity. Liebigs Ann Chem 1991, 1991, 1273. <http://dx.doi.org/10.1002/jlac.1991199101219>
  • Sugai Takeshi, Yokochi Tomoki, Watanabe Naoyuki, Ohta Hiromichi: A synthetic study of (−)-dihydroedulan II and related compounds. Tetrahedron 1991, 47, 7227. <http://dx.doi.org/10.1016/S0040-4020(01)89725-8>
  • Rosini Goffredo, Marotta Emanuela, Raimondi Andrea, Righi Paolo: Resolution and EPC synthesis of both enantiomers of 2,5-Dimethylbicyclo[3.2.0]heptan-endo-2-ol, Key Intermediate in the Synthesis of Grandisol. Tet Asymm 1991, 2, 123. <http://dx.doi.org/10.1016/S0957-4166(00)80532-7>
  • Schwab Elisabeth, Bernreuther Alexander, Puapoomchareon Prapai, Mori Kenji, Schreier Peter: Stereoselective formation of metabolites from 2-methyl-2-hepten-6-one by Botrytis cinerea. Tet Asymm 1991, 2, 471. <http://dx.doi.org/10.1016/S0957-4166(00)82172-2>
  • Mori Kenji, Puapoomchareon Prapai: Pheromone Synthesis, CXVI Conversion of the Enantiomers of Sulcatol to the Enantiomers ofcis-Pityol, a Volatile Compound from the Elm Bark BeetlePteleobius vittatus. Liebigs Ann Chem 1989, 1989, 1261. <http://dx.doi.org/10.1002/jlac.1989198902100>
  • Francke Wittko, Schulz Stefan, Sinnwell Volker, König Wilfried A., Roisin Yves: Epoxytetrahydroedulan, a New Terpenoid from the Hairpencils ofEuploea (Lep.: Danainae) Butterflies. Liebigs Ann Chem 1989, 1989, 1195. <http://dx.doi.org/10.1002/jlac.198919890291>