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Collect. Czech. Chem. Commun. 1979, 44, 558-588
https://doi.org/10.1135/cccc19790558

In situ reactions with trichloroacetyl isocyanate and their application to structural assignment of hydroxy compounds by 1H NMR spectroscopy. A general comment

Zdeněk Samek and Miloš Buděšínský

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6

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  • Shen Shou-Mao, Appendino Giovanni, Guo Yue-Wei: Pitfalls in the structural elucidation of small molecules. A critical analysis of a decade of structural misassignments of marine natural products. Nat. Prod. Rep. 2022, 39, 1803. <https://doi.org/10.1039/D2NP00023G>
  • van Den Berge L., Tavernier D., Anteunis M.: Synthesis of α-(2-Hydroxy-2, 2-Dimethylethyl)-ω-Methyl-, and of α ω-Bis (2-Hydroxy-2,2-Dimethylethyl) Polyethylene Glycol. Bull. Soc. Chim. Belges 2010, 95, 269. <https://doi.org/10.1002/bscb.19860950407>
  • van Den Berge L., van Damme S., Anteunis M. J. O., Tavernier D.: The Preparation of α-Hydro-ω-Hydroxypoly(Oxyethane-1,2-Diyl) Ditosylate (Peg(OTs)2) Revisited. Bull. Soc. Chim. Belges 2010, 100, 115. <https://doi.org/10.1002/bscb.19911000203>
  • Samek Z., Holub M., Bloszyk E., Drozdż B.: Über die Struktur von Schkuhriolid - einem neuen Lacton aus Schkuhria schkuhrioides (LINK et OTTO) THELLUNG. Z. Chem. 2010, 19, 449. <https://doi.org/10.1002/zfch.19790191211>
  • Dombi György, Tresselt Dieter, Schönecker Bruno: 1H-NMR-Untersuchungen mit Trichloracetylisocyanat; Lösungsmittel-, Konzentrations- und Temperaturabhängigkeit des NH-Protonensignals von Trichloracetylcarbamoyl-Verbindungen. Z. Chem. 2010, 20, 61. <https://doi.org/10.1002/zfch.19800200215>
  • Buděšínský Miloš, Vokáč Karel, Harmatha Juraj, Cvačka Josef: Additional minor ecdysteroid components of Leuzea carthamoides. Steroids 2008, 73, 502. <https://doi.org/10.1016/j.steroids.2007.12.021>
  • Harmatha Juraj, Buděšínský Miloš, Vokáč Karel, Pavlík Milan, Grüner Karel, Laudová Věra: Lignan Glucosides and Serotonin Phenylpropanoids from the Seeds of Leuzea carthamoides. Collect. Czech. Chem. Commun. 2007, 72, 334. <https://doi.org/10.1135/cccc20070334>
  • Juárez Ernesto, García Adriana, Hommer Herbert, Salas Magali, Gordillo Barbara: Stereoselective synthesis and conformational analysis of aromaticC-thionucleosides. Heteroatom Chem. 2006, 17, 289. <https://doi.org/10.1002/hc.20205>
  • Buděšínský Miloš, Fajkoš Jan, Günter Jaroslav, Kasal Alexander: Synthesis, Reactions, Conformation Analysis, and NMR Spectra of 5,10-Epoxy-5ξ,10ξ-estrane-3,17-diones. Collect. Czech. Chem. Commun. 2005, 70, 507. <https://doi.org/10.1135/cccc20050507>
  • Chodounská Hana, Pouzar Vladimı́r, Buděšı́nský Miloš, Slavı́ková Barbora, Kohout Ladislav: Synthesis of 3-methyl-3-hydroxy-6-oxo-androstane derivatives. Steroids 2004, 69, 605. <https://doi.org/10.1016/j.steroids.2004.04.007>
  • Šíša Miroslav, Buděšínský Miloš, Kohout Ladislav: Synthesis and Biological Activity of 7a-Homo- and 7a,7b-Dihomo-5α-cholestane Analogues of Brassinolide. Collect. Czech. Chem. Commun. 2003, 68, 2171. <https://doi.org/10.1135/cccc20032171>
  • Ajaj Khalid Abu, Hennig Lothar, Findeisen Matthias, Giesa Sabine, Müller Dietrich, Welzel Peter: Synthesis of a complex disaccharide precursor of phosphonate analogues of the antibiotic moenomycin A12. Tetrahedron 2002, 58, 8439. <https://doi.org/10.1016/S0040-4020(02)01049-9>
  • Reyes-Trejo Benito, Joseph-Nathan Pedro: Modhephene derivatives from Pluchea sericea. Phytochemistry 1999, 51, 75. <https://doi.org/10.1016/S0031-9422(98)00634-7>
  • Quijano Leovigildo, Nuñez Isabel S., Fronczek Frank R., Fischer Nikolaus H.: A guaianolide and four melampolides from Melampodium leucanthum. Phytochemistry 1997, 45, 769. <https://doi.org/10.1016/S0031-9422(97)00025-3>
  • Appendino Giovanni, Jakupovic Jasmin, Cravotto Giancarlo, Biavatti-Weber Maique: The reaction of 6,8-disubstituted E,E-germacra-1(10),4-diene 4-epoxides with oxyphilic reagents. Tetrahedron 1997, 53, 4681. <https://doi.org/10.1016/S0040-4020(97)00137-3>
  • Trnka Tomáš, Buděšínský Miloš, Černý Miloslav: Improved preparation of 1,6-anhydro-4-deoxy-2-O-p-toluenesulphonylβ-d-xylo-hexopyranose and of its d-[4-2H]gluco-analogue from 1,6 : 3,4-dianhydro-2-O-p-toluenesulphonyl-β-d-galactopyranose. Carbohydrate Research 1994, 259, 131. <https://doi.org/10.1016/0008-6215(94)84203-5>
  • Pouzar Vladimír, Fajkoš Jan: Synthesis of (19E)-3β,17-dihydroxy-20-oxopregn-5-en-19-al 19-(O-carboxymethyl)oxime, new steroidal hapten for 17-hydroxypregnenolone. Steroids 1994, 59, 696. <https://doi.org/10.1016/0039-128X(94)90101-5>
  • Píš Jaroslav, Buděšínsky̌ Miloš, Vokáč Karel, Laudová Věra, Harmatha Juraj: Ecdysteroids from the roots of Leuzea carthamoides. Phytochemistry 1994, 37, 707. <https://doi.org/10.1016/S0031-9422(00)90343-1>
  • Appendino Giovanni, Varese Marcella, Gariboldi Pierluigi, Gabetta Bruno: A new rearrangement of oxetane-type taxoids. Tetrahedron Letters 1994, 35, 2217. <https://doi.org/10.1016/S0040-4039(00)76801-8>
  • Barboni Luciano, Gariboldi Pierluigi, Torregiani Elisabetta, Appendino Giovanni, Cravotto Giancarlo, Bombardelli Ezio, Gabetta Bruno, Viterbo Davide: Chemistry and occurrence of taxane derivatives. Part 16. Rearranged taxoids from Taxus×media Rehd. cv Hicksii. X-Ray molecular structure of 9-O-benzoyl-9,10-dide-O-acetyl-11(15 → 1)abeo-baccatin VI. J. Chem. Soc., Perkin Trans. 1 1994, 3233. <https://doi.org/10.1039/P19940003233>
  • Möller Uwe, Hobert Kurt, Donnerstrag Astrid, Wagner Petra, Müller Dietrich, Fehlhaber Hans-Wolfram, Markus Astrid, Welzel Peter: Moenomycin A - Structure-activity relations synthesis of the D-galacturonamide analogue of the smallest antibiotically active degradation product of moenomycin A. Tetrahedron 1993, 49, 1635. <https://doi.org/10.1016/S0040-4020(01)80351-3>
  • Appendino Giovanni, Özen Hasan Çetin, Gariboldi Pierluigi, Torregiani Elisabetta, Gabetta Bruno, Nizzola Rita, Bombardelli Ezio: New oxetane-type taxanes from Taxus wallichiana Zucc. J. Chem. Soc., Perkin Trans. 1 1993, 1563. <https://doi.org/10.1039/P19930001563>
  • Roos Gregory H. P., Manickum Thavrin, Malissar Dean G.: A Facile Diagnostic 1 H NMR Method for Syn and anti Hydroxy Systems. Jnl Chinese Chemical Soc 1992, 39, 105. <https://doi.org/10.1002/jccs.199200016>
  • Appendino Giovanni, Özen Hasan Cetin, Nano Gian Mario, Cisero Marco: Sesquiterpene coumarin ethers from the genus Heptaptera. Phytochemistry 1992, 31, 4223. <https://doi.org/10.1016/0031-9422(92)80447-M>
  • Reher Gesa, Buděšínský Miloš: Triterpenoids from plants of the sanguisorbeae. Phytochemistry 1992, 31, 3909. <https://doi.org/10.1016/S0031-9422(00)97552-6>
  • Ochir G., Buděšínský M., Motl O.: 3-oxa-guaianolides from Achillea millefolium. Phytochemistry 1991, 30, 4163. <https://doi.org/10.1016/0031-9422(91)83489-8>
  • Delgado Guillermo, Ríos María Yolanda: Monoterpenes from Chrysactinia mexicana. Phytochemistry 1991, 30, 3129. <https://doi.org/10.1016/S0031-9422(00)98268-2>
  • Vargas David, Fronczek Frank R., Ober Alfonso G., Fischer Nikolaus H.: Molecular Structure of the Eudesmanolide Septulinolide. Spectroscopy Letters 1991, 24, 1353. <https://doi.org/10.1080/00387019108021766>
  • Trumtel Michel, Tavecchia Paolo, Veyrières Alain, Sinaÿ Pierre: Syntheses of trisaccharide CDE and tetrasaccharide BCDE fragments found in orthosomycins. Carbohydrate Research 1990, 202, 257. <https://doi.org/10.1016/0008-6215(90)84084-8>
  • Fukuzawa Akio, Aye Mya, Takaya Yoshiaki, Masamune Tadashi, Murai Akio: A sesquiterpene alcohol from the red alga Laurencia nipponica. Phytochemistry 1990, 29, 2337. <https://doi.org/10.1016/0031-9422(90)83067-B>
  • Maruyama Masao: Sesquiterpene lactones from Carpesium divaricatum. Phytochemistry 1990, 29, 547. <https://doi.org/10.1016/0031-9422(90)85115-V>
  • Schraml Jan: 29Si N M R spectroscopy of trimethylsilyl tags. Progress in Nuclear Magnetic Resonance Spectroscopy 1990, 22, 289. <https://doi.org/10.1016/0079-6565(90)80010-F>
  • Vereshchagin A. L., Anikina E. V., Syrchina A. I., Lapin M. F., Azin L. A., Semenov A. A.: Chemical investigation of the bitter substances of the fruit of Lonicera caerulea. Chem Nat Compd 1989, 25, 289. <https://doi.org/10.1007/BF00597704>
  • Calderón José S., Quijano Leovigildo, Gómez Federico, Ríos Tirso: Prochamazulene sesquiterpene lactones from Stevia serrata. Phytochemistry 1989, 28, 3526. <https://doi.org/10.1016/0031-9422(89)80380-2>
  • Daniewski Wlodzimierz M., Gumulka Maria, Ptaszynska Katarzyna, Vidari Giovanni, Garlaschelli Luigi, Fronza Giovanni, Budĕs̆insky Milos: 8-epi-pipertriol, a lactarane sesquiterpene from Lactarius necator. Phytochemistry 1988, 27, 3315. <https://doi.org/10.1016/0031-9422(88)80053-0>
  • Vasquez Marta, Macias Francisco A., Urbatsch Lowell E., Fischer Nikolaus H.: Sesquiterpenes from Rudbeckia grandiflora. Phytochemistry 1988, 27, 2195. <https://doi.org/10.1016/0031-9422(88)80125-0>
  • Vargas David, Urbatsch Lowell E., Fischer Nikolaus H.: Sesquiterpene lactones from Squamopappus skutchii. Phytochemistry 1988, 27, 1413. <https://doi.org/10.1016/0031-9422(88)80206-1>
  • Hohgardt Heidemarie, Dietrich Wolfgang, Kühne Harald, Müller Dietrich, Grzelak Detlef, Welzel Peter: Synthesis of two structural analogues of the smallest antibiotically active degradation product of moenomycin a. Tetrahedron 1988, 44, 5771. <https://doi.org/10.1016/S0040-4020(01)81436-8>
  • Appendino Giovanni, Hoflack Jan, De Clercq Pierre J., Chiari Giacomo, Calleri Mariano: Intramolecular diels-alder reaction with furan-diene. Comparison of reactivity and stereoselectivity within a set of structurally related substrates of. Tetrahedron 1988, 44, 4605. <https://doi.org/10.1016/S0040-4020(01)86163-9>
  • Ober Alfonso G., Fischer Nikolaus H.: Sesquiterpene lactones from Calea septuplinervia. Phytochemistry 1987, 26, 848. <https://doi.org/10.1016/S0031-9422(00)84803-7>
  • Gantimur D., Syrchina A. I., Semenov A. A.: Khellactone derivatives from Phlojodicarpus sibiricus. Chem Nat Compd 1986, 22, 103. <https://doi.org/10.1007/BF00574597>
  • Ober Alfonso G., Fischer Nikolaus H., Parodi Felix: Jamaicolides A-D, four sesquiterpene lactones from Calea jamaicensis. Phytochemistry 1986, 25, 877. <https://doi.org/10.1016/0031-9422(86)80020-6>
  • Tanrisever Nesrin, Fronczek Frank R., Fischer Nikolaus H., Williamson G.Bruce: Ceratiolin and other flavonoids from Ceratiola ericoides. Phytochemistry 1986, 26, 175. <https://doi.org/10.1016/S0031-9422(00)81505-8>
  • Valle Maria Grazia, Appendino Giovanni, Nano Gian Mario, Picci Vincenzo: Prenylated coumarins and sesquiterpenoids from Ferula communis. Phytochemistry 1986, 26, 253. <https://doi.org/10.1016/S0031-9422(00)81522-8>
  • Ober Alfonso G., Urbatsch Lowell E., Fischer Nikolaus H.: Sesquiterpene lactones from Calea leptocephala. Phytochemistry 1986, 25, 467. <https://doi.org/10.1016/S0031-9422(00)85502-8>
  • Kočovský Pavel: Carbamates : A method of synthesis and some syntehtic applications. Tetrahedron Letters 1986, 27, 5521. <https://doi.org/10.1016/S0040-4039(00)85256-9>
  • Kloosterman Marcel, De Nijs Mark P., Van Boom Jacques H.: Synthesis of 1,6-Anhydro-2-O-trifluoromethanesulphonyl-0-D-mannopyranose Derivatives and Their Conversion Into the Corresponding 1.6-Anhydro-2-azido-2-deoxy-β-D-glucopyranoses: A Convenient and Efficient Approach. Journal of Carbohydrate Chemistry 1986, 5, 215. <https://doi.org/10.1080/07328308608062961>
  • Kloosterman M., Kuyl-Yeheskiely E., van Boom J. H.: Reductive introduction and oxidative removal of the 4-methoxybenzyl ether in the presence of the azido group. Synthesis of 2-azido-2-deoxy sugars having chain extension at C-4. Recl. Trav. Chim. Pays-Bas 1985, 104, 291. <https://doi.org/10.1002/recl.19851041105>
  • Agrawal P.K., Jain D.C., Gupta R.K., Thakur R.S.: Carbon-13 NMR spectroscopy of steroidal sapogenins and steroidal saponins. Phytochemistry 1985, 24, 2479. <https://doi.org/10.1016/S0031-9422(00)80653-6>
  • Ober Alfonso G., Urbatsch Lowell E., Fischer Nikolaus H.: Two guaianolides from calea solidaginea. Phytochemistry 1985, 24, 2728. <https://doi.org/10.1016/S0031-9422(00)80708-6>
  • Mata Rachel, Delgado Guillermo, De Vivar Alfonso Romo: Sesquiterpene lactones of artemisia klotzchiana. Phytochemistry 1985, 24, 1515. <https://doi.org/10.1016/S0031-9422(00)81057-2>
  • Pestchanker M.J., Ascheri M.S., Giordano O.S.: Uspallatine, a pyrrolizidine alkaloid from senecio uspallatensis. Phytochemistry 1985, 24, 1622. <https://doi.org/10.1016/S0031-9422(00)81085-7>
  • Talapatra Sunil K., Bose Srabani, Mallik Asok K., Talapatra Bani: On the chemistry of indian orchidaceae plants—II. Tetrahedron 1985, 41, 2765. <https://doi.org/10.1016/S0040-4020(01)96378-1>
  • Schneider Hans-jörg, Agrawal Pawan Kumar: Conformations and13C NMR shifts in tetralins. Org. Magn. Reson. 1984, 22, 180. <https://doi.org/10.1002/mrc.1270220310>
  • Ober Alfonso G., Quijano Leovigildo, Urbatsch Lowell E., Fischer Nikolaus H.: Guaianolides from Calea subcordata. Phytochemistry 1984, 23, 1289. <https://doi.org/10.1016/S0031-9422(00)80443-4>
  • Delgado Guillermo, de Vivar Alfonso Romo, Cárdenas Jorge, Pereda-Miranda Rogelio, Huerta Eduardo: Ent-beyerene and ent-atisene diterpenes from viguiera insignis. Phytochemistry 1984, 23, 2285. <https://doi.org/10.1016/S0031-9422(00)80536-1>
  • Appendino Giovanni, Gariboldi Pierluigi, Nano Gian Mario, Tétényi Péter: Tetrahydrofuran-type terpenoids from Tanacetum vulgare. Phytochemistry 1984, 23, 2545. <https://doi.org/10.1016/S0031-9422(00)84096-0>
  • Teresa J. de Pascual, Grande C., Moran J. R., Grande M.: A REVISED STRUCTURE FOR DITERPENOID MAGYDARDIENDIOL. Chem. Lett. 1984, 13, 247. <https://doi.org/10.1246/cl.1984.247>
  • Appendino Giovanni, Gariboldi Pierluigi, Mario Nano Gian: Tanacetols A and B, non-volatile sesquiterpene alcohols, from Tanacetum vulgare. Phytochemistry 1983, 22, 509. <https://doi.org/10.1016/0031-9422(83)83035-0>
  • Appendino Giovanni, Gariboldi Pierluigi, Mario Nano Gian: Isomeric hydroperoxyeudesmanolides from Artemisia umbelliformis. Phytochemistry 1983, 22, 2767. <https://doi.org/10.1016/S0031-9422(00)97692-1>
  • Nemec Josef, Rhoades Jerry M.: Regiochemical Aspects in Reactions of 6-Azauridine Dialdehyde. Nucleosides and Nucleotides 1983, 2, 99. <https://doi.org/10.1080/07328318308081252>
  • Appendino Giovanni, Gariboldi Pierluigi: The stereochemistry of matricin and 4-epimatricin, proazulene sesquiterpene lactones from Artemisia arborescens. Phytochemistry 1982, 21, 2555. <https://doi.org/10.1016/0031-9422(82)85255-2>
  • Fuska J., Prousek J., Rosazza J., M. Budesinsky: Microbial transformations of natural antitumor agents. 23. conversion of withaferin-A to 12β- and 15β-hydroxy derivatives of withaferin-A. Steroids 1982, 40, 157. <https://doi.org/10.1016/0039-128X(82)90030-7>
  • Schönecker B., Tresselt D., Schubert G., Ponsold K.: Steroide. 66.1H-NMR-Untersuchungen. Konfigurationszuordnung 15, 16, 17-trisubstituierter Steroide. J. Prakt. Chem. 1981, 323, 207. <https://doi.org/10.1002/prac.19813230205>
  • Romo de Vivar A., A.L. Pérez C., C. León N., Delgado G.: 11,13-Dehydroeriolin, schkuhrioidin and schkuhriolid, germacranolides from Schkuhria species. Phytochemistry 1980, 21, 2905. <https://doi.org/10.1016/0031-9422(80)85065-5>
  • Markiewicz Wojciech T., Samek Zdeněk, Smrt Jiří: The reaction of 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane with some open chain polyhydroxy compounds. Tetrahedron Letters 1980, 21, 4523. <https://doi.org/10.1016/S0040-4039(00)74540-0>
  • SAMEK Z., BUDESINSKY M.: ChemInform Abstract: THE IN SITU REACTIONS WITH TRICHLOROACETYL ISOCYANATE AND THEIR APPLICATION TO STRUCTURAL ASSIGNMENT OF HYDROXY COMPOUNDS BY PROTON NMR SPECTROSCOPY. A GENERAL COMMENT. Chemischer Informationsdienst 1979, 10. <https://doi.org/10.1002/chin.197922340>