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Original Articles

New Reactions of the Thiocarbonyl Function. The Synthesis of Hindered Peptides

Pages 1-20 | Published online: 17 Mar 2008

NOTES AND REFERENCES

  • Barton D. H. R. George M. V. Tomoeda M. , J. Chem. Soc. , 1967 ( 1962 ).
  • Xanthate radical chemistry: Delduc P. Tailhan C. Zard S. Z. , J. Chem. Soc., Chem. Commun. , 308 ( 1988 ); J. E. Forbes, C. Tailhan, S. Z. Zard, Tetrahedron Lett., 31, 2565 (1990); J. Axon, L. Boiteau, J. Boivin, J. E. Forbes, S. Z. Zard, Ibid., 35, 1719 (1994). Radical chain reactions of xanthic anhydrides: J. E. Forbes, S. Z. Zard, Tetrahedron Lett., 30, 4367 (1989); Idem, Tetrahedron, 49, 8257 (1993). Radical chain reactions of S-alkoxycarbonyl xanthates: J. E. Forbes, S. Z. Zard, J. Am. Chem. Soc., 112, 2034 (1990). Radical reactions involving S-triphenyltin xanthate: J. Boivin, J. Camara, S. Z. Zard, J. Am. Chem. Soc., 114, 7909 (1992). The non-radical chemistry of S-propargyl xanthates: F. Mestre, C. Tailhan, S. Z. Zard, Heterocycles, 28, 171 (1989); J. Boivin, C. Tailhan, S. Z. Zard, J. Am. Chem. Soc., 113, 5874 (1991); J. Boivin, E. B. Henriet, C. Tailhan, S. Z. Zard, Tetrahedron Lett., 34, 2763 (1993); J. Boivin, E. B. Henriet, S. Z. Zard, J. Am. Chem. Soc., 116, 9739 (1994); Idem, Tetrahedron Lett., 36, 5171 (1995); M. A. Poelert, S. Z. Zard, Synlett., 325 (1995); M. A. Poelert, W. Roger, S. Z. Zard, J. Chem. Soc., Chem. Commun., 743 (1996) .
  • Achmatowicz S. Barton D. H. R. Magnus P. D. Poulton G. A. West P. J. , J. Chem. Soc., Perkin Trans. 1 , 1567 ( 1973 ); D. H. R. Barton, M. Bolton, P. D. Magnus, K. G. Marathe, G. A. Poulton, P. J. West, Ibid., 1574 (1973).
  • Barton D. H. R. Bolton M. Magnus P. D. West P. J. Porter G. Wirz J. , J. Chem. Soc., Chem. Commun. , 632 ( 1972 )
  • Barton D. H. R. Guziec F. S. Shahak I. , J. Chem. Soc., Perkin Trans. 1 , 1794 ( 1974 ); T. G. Back, D. H. R. Barton, M. R. Britten-Kelly, F. S. Guziec, Ibid., 2079 (1976) .
  • See, also: Kellogg R. M. Wassenaar S. , Tetrahedron Lett. , 1987 ( 1970 ); R. M. Kellogg, S. Wassenaar, J. Buter, Ibid., 4689 (1970); J. Buter, S. Wassenaar, R. M. Kellogg, J. Org. Chem., 37, 4045 (1972) .
  • Amongst others, see: Staudinger H. Siegwart J. , Helv. Chim. Acta , 3 , 833 ( 1920 ); A. Schönberg, B. König, E. Singer, Chem. Ber., 100, 767 (1967); W. J. Middleton, J. Org. Chem., 34, 3201 (1969) .
  • For reviews on sterically strained organic molecules (tetra-t-butylethylene, inter alia), see: Liebman J. F. Greenberg A. , Chem. Rev. , 76 , 311 ( 1976 ); T. T. Tidwell, Tetrahedron, 34, 1855 (1978) .
  • For recent attempts at the synthesis of tetra-t-butylethylene, see: Guziec F. S. Murphy C. J. , J. Org. Chem. , 45 , 2890 ( 1980 ); E. R. Cullen, F. S. Guziec, Ibid., 51, 1212 (1986). Also, see: F. S. Guziec, L. J. Sanfilippo, Tetrahedron, 44, 6241 (1988) and the references therein .
  • Barton D. H. R. McCombie S. W. , J. Chem. Soc., Perkin Trans. 1 , 1574 ( 1975 ).
  • Barton D. H. R. Crich D. Motherwell W. B. , J. Chem. Soc., Chem. Commun. , 939 ( 1983 ); Idem, Tetrahedron, 41, 3901 (1985) .
  • Barton D. H. R. Blundell P. Jaszberenyi Cs.J. , J. Am. Chem. Soc. , 113 , 6937 ( 1991 ).
  • Barton D. H. R. Tachdjian C. , Tetrahedron , 48 , 7091 ( 1992 ); D. H. R. Barton, P. Blundell, J. Cs. Jaszberenyi, Ibid., 48, 7121 (1992) .
  • Barton D. H. R. Ferreira J. A. , Tetrahedron , 52 , 0000 ( 1996 ), in press.
  • The first article in this series of two addresses the technical details of the concerted reaction, whilst the second article is concerned with applications in peptide chemistry . The present paper represents an abridgment of the original two articles.
  • De Almeida M. V. Barton D. H. R. Bytheway I. Ferreira J. A. Hall M. B. Liu W. Taylor D. K. Thomson L. , J. Am. Chem. Soc. , 117 , 4870 ( 1995 ).
  • Crawford R. J. Raap R. , J. Org. Chem. , 28 , 2419 ( 1963 ).
  • Cooley J. H. Mosher M. W. Khan M. A. , J. Am. Chem. Soc. , 90 , 1867 ( 1968 ).
  • Buccigross J. M. Glover S. A. Hammond G. P. Rowbottom C. A. , Aust. J. Chem. , 48 , 353 ( 1995 ).
  • Buccigross J. M. Glover S. A. , J. Chem. Soc., Perkin Trans. 2 , 595 ( 1995 ).
  • Barton D. H. R. Liu W. , unpublished results.
  • Newcomb M. , Tetrahedron , 49 , 1151 ( 1993 ).
  • Oae , S. and Doi , J. T. 1991 . “ This intramolecular collapse would be another example of ligand coupling within a hypervalent sulfur atom ” . In Organic Sulfur Chemistry: Structure and Mechanism , 183 – 201 . Boca Raton : CRC Press .
  • Mukaiyama T. Ueki M. Maruyama H. Matsueda R. , J. Am. Chem. Soc. , 90 , 4490 ( 1968 ); Ibid., 91, 1554 (1969); M. Ueki, H. Maruyama, T. Mukaiyama, Bull. Chem. Soc. Jpn., 44, 1108 (1971); É. A. Parfenov, V. A. Fomin, J. Gen. Chem. USSR (Engl. Transl.), 51, 947 (1981); Ibid., 51, 961 (1981) .
  • Grieco P. A. , Aldrichimica Acta , 24 , 59 ( 1991 ).
  • Díaz C. Cuevas J. González G. , Z. Anorg. Allg. Chem. , 592 , 7 ( 1991 ).
  • Davis F. A. , Int. J. Sulfur Chem. , 8 , 71 ( 1973 ).
  • Barton D. H. R. Ozbalik N. Vacher B. , Tetrahedron , 44 , 7385 ( 1988 ).
  • The sulfenamides can be accessed through a multitude of ways. For a recent, compendious review, see: Craine L. Raban M. , Chem. Rev. , 89 , 689 ( 1989 ).
  • Trost B. M. , Angew. Chem. Int. Ed. Engl. , 34 , 259 ( 1995 ).
  • Barton D. H. R. Chen C. Wall G. M. , Tetrahedron , 47 , 6127 ( 1991 ).
  • Douglass M. L. , US Patent 4 049 665 , Chem. Abstr. , 88 , 6743f ( 1978 ).
  • Spencer J. R. Antonenko V. V. Delaet N. G. J. Goodman M. , Int. J. Pept. Protein Res. , 40 , 282 ( 1992 ).
  • White D. J. G. (Ed.), Cyclosporin A. Proceedings of an International Conference on Cyclosporin A , Elsevier Biomedical Press Amsterdam ), 1982 .
  • Frérot E. Coste J. Pantaloni A. Dufour M.-N. Jouin P. , Tetrahedron , 47 , 259 ( 1991 ).
  • Bayfield R. F. Cole E. R. , Phosphorus, Sulfur, and Silicon , 45 , 237 ( 1989 ).
  • Carpino L. A. Ionescu D. El-Faham A. , J. Org. Chem. , 61 , 2460 ( 1996 ) and the references there cited.
  • Mukaiyama , T. 1990 . Challenges in Synthetic Organic Chemistry , 75 – 92 . Oxford : Clarendon Press .
  • Barton , D. H. R. , Bridon , D. , Fernandez-Picot , I. and Zard , S. Z. 1987 . “Sodium Omadine®” . Tetrahedron , 43 : 2733 The free acid is readily obtained on acidification with concentrated hydrochloric acid -- N H-thione can be bought from the Olin Corporation as a 40% aqueous solution of the salt, Oxidation of the free acid with 30% aqueous hydrogen peroxide affords 22'-dithiodipyridine-11'-dioxide -- D H R Barton C Chen G M Wall Ibid 47 6127 1991 This dioxide has only recently become commercially available from the Aldrich Chemical Company
  • Barton D. H. R. Samadi M. , Ibid. , 48 , 7083 ( 1992 ).
  • Almasi , L. 1982 . Sulfur in Organic and Inorganic Chemistry , Edited by: Senning , A. Vol. 4 , 47 – 130 . New York : Marcel Dekker .
  • Purcell , K. F. and Kotz , J. C. 1977 . Inorganic Chemistry , 329 – 338 . Japan : Holt Saunders .
  • Overman L. E. Matzinger D. O'Connor E. M. Overman J. D. , J. Am. Chem. Soc. , 96 , 6081 ( 1974 ) and the references there cited.
  • Barton D. H. R. Gero S. D. Negron G. Quiclet-Sire B. Samadi M. Vincent C. , Nucleosides & Nucleotides , 14 , 1619 ( 1995 ). See, for example:
  • Williams M. W. Young G. T. , J. Chem. Soc. , 881 ( 1963 ).
  • Ibid. , 3701 ( 1964 ).
  • Benoiton N. L. Kuroda K. Chen F. M. F. , Int. J. Pept. Protein Res. , 13 , 403 ( 1979 ).
  • We only recently became aware of the fact that, some twenty years ago, Mukaiyama et al. had inadvertently performed the first reaction between a free amine and what is now called a Barton PTOC ester. By application of oxidation-reduction condensation, the Barton PTOC ester-amine combination was shown to afford tetrapeptides in high yield and to preserve optical integrity. The coupling reaction was also shown to be effective in solution and on solid support. See, for example: Matsueda R. Takahagi H. Mukaiyama T. , Chem. Lett. , 1977 ( 719 ) and the references there cited.
  • Paquette L. A. , J. Am. Chem. Soc. , 87 , 5186 ( 1965 ); E. C. Taylor, F. Kienzle, A. McKillop, J. Org. Chem., 35, 1672 (1970) .
  • Beckwith , A. L. J. 1970 . The Chemistry of Amides , Edited by: Zabicky , J. 73 – 185 . London : Interscience Publishers . B C Challis J A Challis Comprehensive Organic Chemistry Eds D H R Barton W D Ollis Pergamon Press Oxford 1979 Volume 2 Chapter 99 pp 957-986

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