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Synlett 2009(7): 1034-1040
DOI: 10.1055/s-0028-1088219
DOI: 10.1055/s-0028-1088219
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New York
The Use of Butyl Organotellurides in the Synthesis of Natural Bioactive Compounds
Further Information
Received
22 June 2008
Publication Date:
20 March 2009 (online)
Publication History
Publication Date:
20 March 2009 (online)
Abstract
The use of organotellurides as precursors of organometallic compounds and as counterparts in catalyzed cross-coupling reactions in the total synthesis of natural bioactive products is presented.
1 Introduction
2 Tellurium-Lithium Exchange Reactions
3 Tellurium-Copper Exchange Reactions
4 Cross-Coupling Reactions Based on Organotellurides
5 Final Considerations
Key words
organometallic reagents - cross-coupling - natural products - tellurides
- 1
Wöhler F. Justus Liebigs Ann. Chem. 1840, 35: 111 - For books, see:
-
2a
Irgolic KJ. The Organic Chemistry of Tellurium Gordon and Breach Science; New York: 1974. -
2b
Patai S. The Chemistry of Organic Selenium and Tellurium Compounds Vol. 2: Wiley; New York: 1987. -
2c
Irgolic KJ. Houben-Weyl Methods of Organic Chemistry: Organotellurium Compounds Vol. E12b:Klamann D. Thieme; Stuttgart: 1990. -
2d
Petragnani N. Tellurium in Organic Synthesis Academic; London: 1994. -
2e
Petragnani N.Stefani HA. Best Synthetic Methods: Tellurium in Organic Synthesis 2nd ed.: Academic; London: 2007. -
2f
Comasseto JV.Clososki GC.Cunha RLOR. In Comprehensive Organometallic Chemistry 3rd ed., Vol. 9:Mingos DMP.Crabtree RH. Elsevier; Amsterdam: 2007. p.587 - For reviews, see:
-
3a
Sadekov ID.Bushkov AY.Minkin VI. Russ. Chem. Rev. (Engl. Transl.) 1979, 48: 635 -
3b
Petragnani N.Stefani HA. Tetrahedron 1995, 61: 1613 -
3c
Comasseto JV.Barrientos-Astigarraga RE. Aldrichimica Acta 2000, 33: 66 -
3d
Zeni G.Lüdtke DS.Panatieri RB.Braga AL. Chem. Rev. 2006, 106: 1032 - For papers, see:
-
4a
Petragnani N. Ann. N. Y. Acad. Sci. 1972, 192: 10 -
4b
Irgolic KJ. J. Organomet. Chem. 1975, 103: 91 -
4c
Fringuelli F.Marino G.Taticchi A. Adv. Heterocycl. Chem. 1977, 21: 119 -
4d
Irgolic KJ.
J. Organomet. Chem. 1977, 130: 411 -
4e
Irgolic KJ. J. Organomet. Chem. 1980, 203: 367 -
4f
Uemura S.
J. Synth. Org. Chem., Jpn. 1983, 41: 804 -
4g
Engman L. Acc. Chem. Res. 1985, 18: 274 -
4h
Petragnani N.Comasseto JV. Synthesis 1986, 1 -
4i
Sadekov ID.Rybalkina LE.Movshovich DY.Bulgarevich SB.Kogan VA. Usp. Khim. 1991, 60: 1229 -
4j
Petragnani N.Comasseto JV. Synthesis 1991, 793 -
4k
Petragnani N.Comasseto JV. Synthesis 1991, 897 -
4l
Comasseto JV. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67: 183 -
4m
Comasseto JV.Ling LW.Petragnani N.Stefani HA. Synthesis 1997, 373 - 5
Reich HJ.Green DP.Phillips NH.Borst JP.Reich IL. Phosphorus, Sulfur Silicon Relat. Elem. 1992, 67: 83 -
6a
Hiiro T.Kambe N.Ogawa A.Miyoshi N.Murai S.Sonoda N. Angew. Chem. Int. Ed. Engl. 1987, 26: 1187 -
6b
Barros SM.Comasseto JV.Berriel JN. Tetrahedron Lett. 1989, 30: 7353 -
6c
Dabdoub MJ.Dabdoub VB.Comasseto JV. Tetrahedron Lett. 1992, 33: 2261 - 7
Dos Santos AA.Ferrarini RS.Princival JL.Comasseto JV. Tetrahedron Lett. 2006, 47: 8933 - 8
Kinzer GW.Fentiman FA.Page FT.Foltz RL.Vite JP.Pitman GG. Nature (London) 1969, 221: 477 -
9a
Zhou J.Ross DW.Niwa CG. Environ. Entomol. 2001, 30: 993 -
9b
Allison JD.Borden JH.McIntosh RL.De Groot P.Gries R. J. Chem. Ecol. 2001, 27: 633 -
10a
Rasmussen LEL.Greenwood DR. Chem. Senses 2003, 28: 433 -
10b
Greenwood DR.Comeskey D.Hunt MB.Rasmussen LEL. Nature (London) 2005, 438: 1097 - 11
Dos Santos AA.Ferrarini RS.Princival JL.Comasseto JV. J. Braz. Chem. Soc. 2008, 19: 811 - 12
Mori K.Sew Y.-B. Tetrahedron 1985, 41: 3429 - 13
Vité JP.Billings RF.Ware CW.Mori K. Naturwissenschaften 1985, 72: 99 - 14
Dos Santos AA.Da Costa CE.Princival JL.Comasseto JV. Tetrahedron: Asymmetry 2006, 17: 2252 - 15
Genovese A.Gambuti A.Piombino P.Moio L. Food Chem. 2007, 103: 1228 - 16
Caccioni RL.Tonini G.Guizzardi M. Z. Pflanzenkr. Pflanzenschutz 1995, 102: 518 - 17
Kuroda M.Yoshida D.Mizusaki S. Agric. Biol. Chem. 1986, 50: 243 - 18
Juvonen RO.Gynther J.Pasanen M.Alhava E.Poso A. Xenobiotica 2000, 30: 81 - 19
Dos Santos AA.Princival JL.Comasseto JV.Barros SMG.Brainer Neto JE. Tetrahedron 2007, 63: 5167 - 20
ter Heide R.Schaap H.Wobben HJ.De Valois PJ.Timmer R. Flavor Constituents in Rum; Qual. Foods Beverages: Chem. Technol. (Proc. 2nd Symp. Int. Flavor Conf.) Academic Press; New York: 1981. 1: p.183 - 21
Dos Santos AA.Castelani P.Bassora BK.Fogo JC.Costa CE.Comasseto JV. Tetrahedron 2005, 61: 9173 - 22
Bassora BK.Da Costa CE.Gariani RA.Comasseto JV.Dos Santos AA. Tetrahedron Lett. 2007, 48: 1485 - 23
Nijhoff WA.Bosboom MA.Smidt MH.Peters WHM. Carcinogenesis 1995, 16: 607 - 24
Wattenberg LW.Lam LKT.Fladmoe AV. Cancer Res. 1979, 39: 1651 - 25
Catalogue
of Flavors and Fragrances
Aldrich;
Milwaukee WI:
1998-1999.
-
26a
Matheus CJ.Taylor J.Tyte MJ.Worthington PA. Synlett 2005, 538 -
26b
Pour M.Špulák M.Balšánek V.Kuneš J.Buchta V.Waisser K. Bioorg. Med. Chem. Lett. 2000, 10: 1893 - 27
Amonkar CP.Tilve SG.Parameswaran PS. Synthesis 2005, 2314 - 28
Yang J.Cohn T.Romo D. Org. Lett. 2000, 2: 763 - 29
Seki T.Satake M.Mackenzie L.Kaspar HF.Yasumoto T. Tetrahedron Lett. 1995, 36: 7093 - 30
Stefani HA.Costa IM.Zeni G. Tetrahedron Lett. 1999, 40: 9215 - 31
Fusetani N.Toyoda T.Asai N.Matsunaga S.Maruyama T. J. Nat. Prod. 1996, 59: 796 -
32a
Barrientos-Astigarraga RE.Castelani P.Sumida CY.Comasseto JV. Tetrahedron Lett. 1999, 40: 7717 -
32b
Comasseto JV.Berriel JN. Synth. Commun. 1990, 20: 1681; corrigendum: Synth. Commun. 1992, 22, 2431 -
32c
Tucci FC.Chieffi A.Comasseto JV. Tetrahedron Lett. 1992, 33: 5721 -
32d
Marino JP.Tucci FC.Comasseto JV. Synlett 1993, 761 -
32e
Tucci FC.Chieffi A.Comasseto JV.Marino JP. J. Org. Chem. 1996, 61: 4975 -
32f
Barrientos-Astigarraga RE.Moraes DN.Comasseto JV. Tetrahedron Lett. 1999, 40: 265 -
32g
Araujo MA.Barrientos-Astigarraga RE.Ellensohn RM.Comasseto JV. Tetrahedron Lett. 1999, 40: 5115 -
32h
Moraes DN.Barrientos-Astigarraga RE.Castelani P.Comasseto JV. Tetrahedron 2000, 56: 3327 -
32i
Castelani P.Comasseto JV. Organometallics 2003, 22: 2108 -
32j
Castelani P.Comasseto JV. J. Braz. Chem. Soc. 2004, 15: 461 - 33
Marino JP.McClure MS.Holub DP.Comasseto JV.Tucci FC. J. Am. Chem. Soc. 2002, 124: 1664 - 34
Zeni G.Panatieri RB.Lissner E.Menezes PH.Braga AL.Stefani HA. Org. Lett. 2001, 3: 819 - 35
Zeni G.Braga AL.Stefani HA. Acc. Chem. Res. 2003, 36: 731 - 36
Kraus CM.Neszmélyi A.Holly S.Wiedemann B.Nenninger A.Torssell KBG.Bohlin L.Wagner H. J. Nat. Prod. 1998, 61: 422 - 37
Redl K.Breu W.Davis B.Bauer R. Planta Med. 1994, 60: 58 - 38
Oliveira JM.Zeni G.Malvestiti I.Menezes PH. Tetrahedron Lett. 2006, 47: 8183 - 39
Resch M.Heilmann J.Steigel A.Bauer R. Planta Med. 2001, 67: 437 - 40
Nishikawa Y.Yasuda I.Watanabe Y.Seto T. Yakugaku Zasshi 1976, 96: 1322 - 41
Najima K,Yanagisawa T,Iimura F, andMihashi H. inventors; JP 4208222 (A). -
42a
Witzgall P.Tasin M.Buser H.-R.Wegner-Kiss G.Mancebon VSM.Ioriatti C.Baeckman A.-C.Bengtsson M.Lehmann L.Francke W. J. Chem. Ecol. 2005, 31: 2923 -
42b
Buser HR.Rauscher S.Arn H.
Z. Naturforsch., C 1974, 29: 781 - 43
Diego DG.Cunha RLOR.Comasseto JV. Tetrahedron Lett. 2006, 47: 7147 - 44
Alves D.Nogueira CW.Zeni G. Tetrahedron Lett. 2005, 46: 8761 - 45
Dabdoub MJ.Begnini ML.Cassol TM.Guerrero PG.Silveira C. Tetrahedron Lett. 1995, 36: 7623 - 46
Naidoo LAC.Drewes SE.Drewes FE.Van Staden J.Aken ME. S. Afr. J. Sci. 1994, 90: 359