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Pure Appl. Chem., 1986, Vol. 58, No. 5, pp. 675-684

http://dx.doi.org/10.1351/pac198658050675

Invention of new reactions useful in the chemistry of natural products

D. H. R. Barton and S. Z. Zard

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  • Murai Koichi, Katoh Shun-ichiroh, Urabe Daisuke, Inoue Masayuki: A radical-based approach for the construction of the tetracyclic structure of resiniferatoxin. Chem. Sci. 2013, 4, 2364. <http://dx.doi.org/10.1039/c3sc50329a>
  • Pimpalpalle Tukaram M., Yin Jian, Linker Torsten: Barton radical reactions of 2-C-branched carbohydrates. Biomol Chem 2012, 10, 103. <http://dx.doi.org/10.1039/c1ob06370g>
  • Lalevée Jacques, Tehfe Mohamad Ali, Morlet-Savary Fabrice, Graff Bernadette, Allonas Xavier, Fouassier Jean Pierre: Radical photopolymerization reactions under air upon lamp and diode laser exposure: The input of the organosilane radical chemistry. Progress in Organic Coatings 2011, 70, 83. <http://dx.doi.org/10.1016/j.porgcoat.2010.10.008>
  • Urabe Daisuke, Yamaguchi Hiroki, Inoue Masayuki: Application of α-Alkoxy Bridgehead Radical for Coupling of Oxygenated Carbocycles. Org Lett 2011, 110812094519022. <http://dx.doi.org/10.1021/ol201758a>
  • Saraiva Maurício F., Couri Mara R.C., Le Hyaric Mireille, de Almeida Mauro V.: The Barton ester free-radical reaction: a brief review of applications. Tetrahedron 2009, 65, 3563. <http://dx.doi.org/10.1016/j.tet.2009.01.103>
  • Dietlin C., Allonas X., Morlet-Savary F., Fouassier J. P., Visconti M., Norcini G., Romagnano S.: Investigation of Barton esters as radical photoinitiators. J Appl Polym Sci 2008, 109, 825. <http://dx.doi.org/10.1002/app.26618>
  • Giese Bernd: Stereoselektivität intermolekularer Radikalreaktionen. Angew Chem 2006, 101, 993. <http://dx.doi.org/10.1002/ange.19891010804>
  • Ho Tse-Lok, Chen Chun-Kuei: Formal Synthesis of Vallesamidine. HCA 2006, 89, 249. <http://dx.doi.org/10.1002/hlca.200690027>
  • Garrido Narciso M., Díez David, Domínguez Sara H., García Mercedes, Sánchez M. Rosa, Davies Stephen G.: Asymmetric synthesis of pent-3-yl (R)-6-methyl-cyclohex-1-ene carboxylate. Tet Asymm 2006, 17, 2183. <http://dx.doi.org/10.1016/j.tetasy.2006.06.048>
  • Intramolecular Radical Cyclizations of Dehydroamino Acid Derivatives. Journal of the Korean Chemical Society 2005, 49, 63. <http://dx.doi.org/10.5012/jkcs.2005.49.1.063>
  • Chimiak A., Przychodzen W., Rachon J.: The thiohydroxamate system. Heteroatom Chem 2002, 13, 169. <http://dx.doi.org/10.1002/hc.10017>
  • Masterson Douglas S., Porter Ned A.: Diastereoselective Free Radical Halogenation, Azidation, and Rearrangement of β-Silyl Barton Esters. Org Lett 2002, 4, 4253. <http://dx.doi.org/10.1021/ol0268182>
  • Nicolaou K. C., Vourloumis Dionisios, Winssinger Nicolas, Baran Phil S.: Der Stand der Totalsynthese zu Beginn des 21. Jahrhunderts. Angew Chem 2000, 112, 46. <http://dx.doi.org/10.1002/(SICI)1521-3757(20000103)112:1<46::AID-ANGE46>3.0.CO;2-P>
  • Alam Maksudul M., Ito Osamu: Energy Transfer, Electron Transfer, and Addition Reactions of Triplet State of 1,3-Dihydroimidazole-2-thiones Investigated by Laser Flash Photolysis. Bull Chem Soc Jpn 1999, 72, 339. <http://dx.doi.org/10.1246/bcsj.72.339>
  • Barton Derek H.R., Géro Stéphane D., Holliday Pascale, Quiclet-Sire Béatrice, Zard Samir Z.: A practical decarboxylative hydroxylation of carboxylic acids. Tetrahedron 1998, 54, 6751. <http://dx.doi.org/10.1016/S0040-4020(98)00337-8>
  • Theodorakis Emmanuel A., Xiang Xin, Lee Mindo, Gibson Tony: On the mechanism of photo-induced nucleic acid cleavage using N-aroyloxy-2-thiopyridones. Tetrahetron Lett 1998, 39, 3383. <http://dx.doi.org/10.1016/S0040-4039(98)00509-7>
  • Barton Derek H.R., Fontana Giovanni: The invention of radical reactions. Part XXXVII. A convenient radical synthesis of dialkyl diselenides from carboxylic acids. Tetrahedron 1996, 52, 11163. <http://dx.doi.org/10.1016/0040-4020(96)00665-5>
  • Barton Derek H. R., Fontana Giovanni: Radical Chemistry Based on (+)-cis-Pinononic and (+)-CIS-Pinonic Acids. Synth Common 1996, 26, 1953. <http://dx.doi.org/10.1080/00397919608003550>
  • Cossu Sergio, Lucchi Ottorino De, Durr Richard, Fabris Fabrizio: An Alternative, Inexpensive Preparation of Phenylsulfonylethylene. Synth Common 1996, 26, 211. <http://dx.doi.org/10.1080/00397919608003606>
  • Alam Maksudul M., Watanabe Akira, Ito Osamu: Laser Flash Photolysis of 2,2'-Dithiobls(pyridine N-oxide): Reactivity of N-Oxypyridyl-2-thio Radical. Photchem Photbio 1996, 63, 53. <http://dx.doi.org/10.1111/j.1751-1097.1996.tb02991.x>
  • Barton Derek H.R., Géro Stephane D., Quiclet-Sire Béatrice, Samadi Mohammad: Stereocontrolled radical reactions in carbohydrate and nucleoside chemistry. Tet Asymm 1994, 5, 2123. <http://dx.doi.org/10.1016/S0957-4166(00)86288-6>
  • Anaya Josefa, Barton Derek H.R., Caballero Ma Cruz, Gero Stephan D., Grande Manuel, Laso Nieves M., Hernando José I.M.: The use of radical decarboxylation in the preparation of 1-methylcarbapenem antibiotic precursors from D-glucosamine. Tet Asymm 1994, 5, 2137. <http://dx.doi.org/10.1016/S0957-4166(00)86289-8>
  • Barton Derek H.R., Gateau-Olesker Alice, Géro Stephan D., Lacher Brigitte, Tachdjian Catherine, Zard Samir Z.: Radical decarboxylative alkylation of tartaric acid. Tetrahedron 1993, 49, 4589. <http://dx.doi.org/10.1016/S0040-4020(01)81288-6>
  • Togo Hideo, Aoki Masahiko, Yokoyama Masataka: Reductive addition to electron-deficient olefins with trivalent iodine compounds. Tetrahedron 1993, 49, 8241. <http://dx.doi.org/10.1016/S0040-4020(01)88042-X>
  • Hamdani Mourad, De Jeso Bernard, Deleuze Hervé, Maillard Bernard: Derivatives of the product of Baker's yeast reduction of ethyl 2-alkyl 3-oxobutanoates as precursors of free radical chirons of the 2(S)-hydroxyalkyl moiety. Tet Asymm 1993, 4, 1229. <http://dx.doi.org/10.1016/S0957-4166(00)80232-3>
  • Barton Derek H.R., Camara José, Cheng Xiaoqin, Géro Stephane D., Jaszberenyi Joseph Cs., Quiclet-Sire Beatrice: From carbohydrates to carbocycles: radical routes via Tellurium derivatives. Tetrahedron 1992, 48, 9261. <http://dx.doi.org/10.1016/S0040-4020(01)85616-7>
  • Barton Derek H.R., Tachdjian Catherine: The invention of radical reactions. Part XXVI. New thio- and seleno-hydroxamic acids; radical chemistry of their O-acyl derivatives. Tetrahedron 1992, 48, 7091. <http://dx.doi.org/10.1016/S0040-4020(01)88250-8>
  • Barton Derek H.R., Tachdjian Catherine: The invention of radical reactions. Part XXVII. Modified Julia Synthesis of Olefins Using radical deoxygenation. Tetrahedron 1992, 48, 7109. <http://dx.doi.org/10.1016/S0040-4020(01)88251-X>
  • Barton Derek H.R., Blundell Paul, Jaszberenyi Joseph Cs.: The invention of radical reactions. Part XXVIII a new very photolabile O-acyl thiohydroxamic acid derivative as precursor of carbon radicals. Tetrahedron 1992, 48, 7121. <http://dx.doi.org/10.1016/S0040-4020(01)88252-1>
  • Barton Derek H.R., Jaszberenyi Joseph Cs., Theodorakis Emmanouil A.: The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates. Tetrahedron 1992, 48, 2613. <http://dx.doi.org/10.1016/S0040-4020(01)88524-0>
  • Barton Derek H.R., Géro Stephane D., Quiclet-Sire Béatrice, Samadi Mohammad: New synthesis of sugar, nucleoside and α-amino acid phosphonates. Tetrahedron 1992, 48, 1627. <http://dx.doi.org/10.1016/S0040-4020(01)88721-4>
  • Okada Keiji, Okubo Katsura, Morita Naoto, Oda Masaji: Reductive decarboxylation of N-(acyloxy)phthalimides via redox-initiated radical chain mechanism. Tetrahetron Lett 1992, 33, 7377. <http://dx.doi.org/10.1016/S0040-4039(00)60192-2>
  • Sumi Kenzo, Di Fabio Romano, Hanessian Stephen: The stereocontrolled synthesis of versatile carbapenem intermediates using the Barton O-acyl 2-thiophyridylhydroxamate fragmentation. Tetrahetron Lett 1992, 33, 749. <http://dx.doi.org/10.1016/S0040-4039(00)77706-9>
  • Okano Takashi, Takakura Nobuyuki, Nakano Yuko, Eguchi Shoji: α,α-Difluroalkanecarboxylic acids: a general synthesis via alkyl radical addition to 1,1-dichloro-2,2-difluoroethylene. Tetrahetron Lett 1992, 33, 3491. <http://dx.doi.org/10.1016/S0040-4039(00)92671-6>
  • Togo Hideo, Ishigami Sachiko, Yokoyama Masataka: A Facile Preparative Method of C-Nucleosides. Chem Lett 1992, 1673. <http://dx.doi.org/10.1246/cl.1992.1673>
  • Togo Hideo, Aoki Masahiko, Yokoyama Masataka: Reductive Addition of Alkyl Radical to Phenyl Vinyl Sulfone. Chem Lett 1992, 2169. <http://dx.doi.org/10.1246/cl.1992.2169>
  • Boivin Jean, Crépon (née da Silva) Elisabeth, Zard Samir Z.: Further observations on the thermal stability of N-hydroxy-2-thiopyridone esters: improved decarboxylative radical additions to olefins. Tetrahetron Lett 1991, 32, 199. <http://dx.doi.org/10.1016/0040-4039(91)80854-Y>
  • Barton Derek H.R., Jaszberenyi Joseph Cs., Tachdjian Catherine: Olefin synthesis by radical methods from xanthate, selenobenzoate and thionocarbonate derivatives of β-hydroxy sulfones. Tetrahetron Lett 1991, 32, 2703. <http://dx.doi.org/10.1016/0040-4039(91)85063-B>
  • Lipczynska-Kochany Ewa: The photolability of hydroxamic acids and its importance to the human environment. Sei Total Environ 1991, 100, 469. <http://dx.doi.org/10.1016/0048-9697(91)90388-U>
  • Okada Keiji, Okubo Katsura, Oda Masaji: A simple and convenient photodecarboxylation method of intact carboxylic acids in the presence of aza aromatic compounds. J Photochem Photobiol A Chem 1991, 57, 265. <http://dx.doi.org/10.1016/1010-6030(91)85022-9>
  • Barton Derek H.R., Géro Stephane D., Béatrice Quiclet-Sire, Samadi Mohammad, Vincent Claire: Synthesis of 5′,8-cyclopurine and of 5′,6-cyclodihydropyrimidine nucleosides using intramolecular radical cyclisation based on the aryl telluride radical exchange process. Tetrahedron 1991, 47, 9383. <http://dx.doi.org/10.1016/S0040-4020(01)80885-1>
  • Barton Derek H.R., Boivin Jean, Crépon (née da Silva) Elisabeth, Sarma Jadab, Togo Hideo, Zaid Samir Z.: Decarboxylative radical addition to vinylsulphones and vinylphosphonium bromide: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones. Tetrahedron 1991, 47, 7091. <http://dx.doi.org/10.1016/S0040-4020(01)96163-0>
  • Barton Derek H.R., Jaszberenyi Joseph Cs., Theodorakis Emmanouil A.: O-Sulfinylation of alcohols with methanesulfonyl cyanide or p-toluenesulfonyl cyanide. Tetrahedron 1991, 47, 9167. <http://dx.doi.org/10.1016/S0040-4020(01)96204-0>
  • Boivin Jean, Fouquet Eric, Zard Samir Z.: A new and synthetically useful source of iminyl radicals. Tetrahetron Lett 1991, 32, 4299. <http://dx.doi.org/10.1016/S0040-4039(00)92153-1>
  • Derek H.R., Barton Ching-Yuh Chern, Joseph Jaszberenyi Cs.: Homologation of acids via carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone. (The two-carbon problem). Tetrahetron Lett 1991, 32, 3309. <http://dx.doi.org/10.1016/S0040-4039(00)92693-5>
  • Barton Derek H.R., Jaszberenyi Joseph Cs., Theodorakis Emmanouil A.: Radical nitrile transfer with methanesulfonyl cyanide or p-toluenesulfonyl cyanide to carbon radicals generated from the acyl derivatives of N-hydroxy-2-thiopyridone. Tetrahetron Lett 1991, 32, 3321. <http://dx.doi.org/10.1016/S0040-4039(00)92696-0>
  • Hamdani Mourad, De Jeso Bernard, Deleuze Hervé, Maillard Bernard: Derivatives of the product of Baker's yeast reduction of ethyl acetoacetate as precursors of free radical chirons of the 2(S)-hydroxypropyl moiety. Tet Asymm 1991, 2, 867. <http://dx.doi.org/10.1016/S0957-4166(00)82196-5>
  • Barton Derek H.R., Sas Wojciech: The invention of radical reactions. Part XIX. The synthesis of very hindered quinones. Tetrahedron 1990, 46, 3419. <http://dx.doi.org/10.1016/S0040-4020(01)81512-X>
  • Newcomb Martin, Deeb Thomas M., Marquardt Donald J.: N-hydroxypyridine-2-thione carbamates. IV. A comparison of 5-exo cyclizations of an aminyl radical and an aminium cation radical. Tetrahedron 1990, 46, 2317. <http://dx.doi.org/10.1016/S0040-4020(01)82012-3>
  • H.R. Barton Derek, Csuhai Eva, Ozbalik Nubar: Functionalisation of saturated hydrocarbons. Part xvi. Chemoselective oxidation. Tetrahedron 1990, 46, 3743. <http://dx.doi.org/10.1016/S0040-4020(01)90510-1>
  • Barton Derek H.R., Lee Kyu Wan, Mehl Wolf, Ozbalik Nubar, Zhang Li: Functionalisation of saturated hydrocarbons. Part xvii. Reactivity of carbon-carbon double bonds. Tetrahedron 1990, 46, 3753. <http://dx.doi.org/10.1016/S0040-4020(01)90511-3>
  • Padwa Albert, Murphree S.Shaun, Yeske Philip E.: Synthesis of vinylic and cyclic sulfones via a radical addition-elimination sequence. Tetrahetron Lett 1990, 31, 2983. <http://dx.doi.org/10.1016/S0040-4039(00)89004-8>
  • Barton Derek H.R., Ramesh Manlan: Generation and fate of nondecarboxylating acyloxy radicals derived from the photolysis of acyl derivatives of N-hydroxy-2-thiopyridone. Tetrahetron Lett 1990, 31, 949. <http://dx.doi.org/10.1016/S0040-4039(00)94400-9>
  • Boivin Jean, Crépon (née da Silva) Elisabeth, Zard Samir Z.: N-hydroxy-2-pyridinethione: A mild and convenient source of hydroxyl radicals. Tetrahetron Lett 1990, 31, 6869. <http://dx.doi.org/10.1016/S0040-4039(00)97193-4>
  • Boivin J., da Silva E., Ourisson G., Zard S.Z.: Proof of a radical transannular hydrogen migration in the longifolene series. Tetrahetron Lett 1990, 31, 2501. <http://dx.doi.org/10.1016/S0040-4039(00)97400-8>
  • Giese Bernd: The Stereoselectivity of Intermolecular Free Radical Reactions [New Synthetic Methods (78)]. Angew Chem Int Ed Engl 1989, 28, 969. <http://dx.doi.org/10.1002/anie.198909693>
  • Barton Derek H.R., Bridon Dominique, Zard Samir Z.: The invention of radical reactions. Part XVIII. Decarboxylative radical addition to arsenic, antimony, and bismuth phenylsulphides - a novel synthesis of nor-alcohols from carboxylic acids. Tetrahedron 1989, 45, 2615. <http://dx.doi.org/10.1016/S0040-4020(01)80092-2>
  • Barton Derek H.R., Ozbalik Nubar, Schmitt Martine: Radical chemistry based on (+)-cis-pinonic acid. Tetrahetron Lett 1989, 30, 3263. <http://dx.doi.org/10.1016/S0040-4039(00)99217-7>
  • Liu Zhujin, Xu Feng: Total synthesis of Na-methyl-Δ18-isokoumidine, a possible precursor of the koumine type indole alkaloids. Tetrahetron Lett 1989, 30, 3457. <http://dx.doi.org/10.1016/S0040-4039(00)99271-2>
  • Dauben William G., Kowalczyk Bruce A., Bridon Dominique P.: Light induced halogenative decarboxylation of thiohydroxamic esters. Tetrahetron Lett 1989, 30, 2461. <http://dx.doi.org/10.1016/S0040-4039(01)80425-1>
  • Barton Derek H.R., Boivin Jean, Sarma Jadab, da Silva Elisabeth, Zard Samir Z.: Some further novel transformations of geminal (pyridine-2-thiyl) phenylsulphones. Tetrahetron Lett 1989, 30, 4237. <http://dx.doi.org/10.1016/S0040-4039(01)80699-7>
  • Linz Günter, Weetman John, Abdel Hady A.F., Helmchen Günter: Asymmetric Diels-Alder reactions: EPC-synthesis of a stable sarkomycin precursor (cyclosarkomycin). Tetrahetron Lett 1989, 30, 5599. <http://dx.doi.org/10.1016/S0040-4039(01)93809-2>
  • Barton Derek H. R., Ozbalik Nubar: Radical Reactions Based on the Thione Function. Phosphorus Sulfur Silicon Relat Elem 1989, 43, 349. <http://dx.doi.org/10.1080/10426508908040293>
  • Doak G.O., Freedman Leon D.: Antimony. J Organomet Chem 1988, 351, 25. <http://dx.doi.org/10.1016/0022-328X(88)83165-6>
  • Barton Derek H.R., Lacher Brigitte, Misterkiewicz Boguslaw, Zard Samir Z.: The invention of radical reactions. Tetrahedron 1988, 44, 1153. <http://dx.doi.org/10.1016/S0040-4020(01)85895-6>
  • Barton Deraǩ H.R., Ozbalik Nubar, Vacher Bernard: The invention of radical reactions part XVIII. A convenient solution to the 1-carbon problem (R-CO2H → R-13CO2H). Tetrahedron 1988, 44, 3501. <http://dx.doi.org/10.1016/S0040-4020(01)85980-9>
  • Barton Derek H.R, Ozbalik Nubar, Vacher Bernard: Tetrahedron 1988, 44, 7385. <http://dx.doi.org/10.1016/S0040-4020(01)86234-7>
  • Patel Vinod F., Pattenden Gerald: Free radical reactions initiated by organocobalt complexes. A new method for the degradation of carboxylic acids tofunctionalised nor-alkanes via acylcobalt salophen intermediates. Tetrahetron Lett 1988, 29, 707. <http://dx.doi.org/10.1016/S0040-4039(00)80190-2>
  • Gilday John P., Paquette Leo A.: Stabilized carbanions by alkyllithium-induced decarboxylation of non-enolizable carboxylic acids. An anionic equivalent to the hunsdiecker reaction. Tetrahetron Lett 1988, 29, 4505. <http://dx.doi.org/10.1016/S0040-4039(00)80532-8>
  • Barton Derek H.R., Ozbalik Nubar, Sarma Jadab C.: The role of organic tellurides as accumulators and exchangers of carbon radicals. Tetrahetron Lett 1988, 29, 6581. <http://dx.doi.org/10.1016/S0040-4039(00)82402-8>
  • Barton Derek H.R., Ozbalik Nubar, Ramesh Manian: Alkylation of amines using trivalent bismuth derivatives. Tetrahetron Lett 1988, 29, 857. <http://dx.doi.org/10.1016/S0040-4039(00)82466-1>
  • Barton Derek H.R., Bridon Dominique, Zardb Samir Z.: The invention of radical chain reactions. Tetrahedron 1987, 43, 5307. <http://dx.doi.org/10.1016/S0040-4020(01)87707-3>
  • H.R. Barton Derek, Lacher Brigitte, Zard Samir Z.: The invention of radical reactions. Tetrahedron 1987, 43, 4321. <http://dx.doi.org/10.1016/S0040-4020(01)90307-2>
  • Crich David, Davies John W.: Stereoselectivity in free radical reactions. Tetrahetron Lett 1987, 28, 4205. <http://dx.doi.org/10.1016/S0040-4039(00)95580-1>
  • Castagnino Enzo, Corsano Stefano, Barton Derek H.R, Zard Samir Z: Decarboxylative radical addition onto protonated heteroaromatic systems including purine bases. Tetrahetron Lett 1986, 27, 6337. <http://dx.doi.org/10.1016/S0040-4039(00)87802-8>
  • Barton Derek H.R, Bridon Dominique, Zard Samir Z: Radical decarboxylative phosphorylation of carboxylic acids. Tetrahetron Lett 1986, 27, 4309. <http://dx.doi.org/10.1016/S0040-4039(00)94261-8>