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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 7-8
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Original Articles

Efficient Syntheses of (d, l) and (d) Selenomethionine

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Pages 1203-1210 | Received 14 Oct 1988, Published online: 24 Oct 2006

References

  • Krief , A. 1980 . Tetrahedron , 36 : 2531
  • Nicolaou , K. C. and Petasis . 1984 . Selenium in Natural Products Synthesis Philadelphia Cis ed
  • Hevesi , L. and Krief , A. 1984 . Janssen Chimica Acta , 2 : 3
  • Liota , D. , ed. 1987 . Organoselenium Chemistry , Chichester, , England : John Wiley .
  • Patai , S. and Rapopport , Z. , eds. 1986 . The Chemistry of Organic Selenium and Tellurium Compounds , Vol. 1 , Chichester, , England : John Wiley . and vol. 2, 1987
  • Klayman , D. L. and Günther , W. H. H. 1973 . Organic Selenium Compounds, their Chemistry and Biology , N. Y. : John Wiley .
  • Shamberger , R. J. 1983 . Biochemistry of Selenium , Edited by: Frieden , E. N. Y. : Plenum Press .
  • Barton , D. H. R. , Bridon , D. , Hervé , Y. , Potier , P. , Thierry , J. and Zard , S. Z. 1986 . Tetrahedron , 42 : 4983 Several syntheses of selenomethionine have been described but many do not fulfill our requirements. For leading references see
  • Ursapharm (Saarbrücken, FRG)
  • Pleninger , H. 1950 . Chem. Ber. , 83 : 265 Under the conditions described in this reference we and others (private communication from Ursapharm) got 14% yield of 3a.
  • Agenäs , L. B. 1965 . Arkiv. Kemi , 29 : 415 For leading references in lactones ring opening by phenyl and benzylselenolates:
  • Agenäs , L. B. and Persson , B. 1967 . Acta Chem. Scand. , 21 : 835 837
  • Detty , M. R. 1978 . Tetrahedron Lett. , : 5087
  • Miyoshi , N. , Ishii , H. , Murai , S. and Sonoda , N. 1979 . Chem. Lett. , : 873
  • Scarborough , R. M. Jr. , Toder , B. H. and Smith , A. B. 1980 . J. Amer. Chem. Soc. , 102 : 3904 and references. cited
  • Liotta , D. , Sunay , U. , Santesteban , H. and Markiewicz , W. 1981 . J. Org. Chem. , 46 : 2605 and references cited
  • Dowd , P. and Kennedy , P. 1981 . Syntethic Commun. , 11 : 935
  • Krief , A. and Trabelsi , M. 1987 . Tetrahedron Lett. , 28 : 4225 and references cited
  • from α-amino-γ-butyrolactone hydrobromide 5,8b and gazeous ammonia in chloroform. Just prepared before to be used
  • Available from Janssen Chimica and Aldrich
  • Günther , W. H. 1966 . J. Org. Chem. , 32 : 1202 Explanation of these differences will be soon described. Dimethyl diselenide has been conveniently prepared in 0.5 kg badges according to the procedure of
  • Obtained in 89% yield from its hydroiodide11 and gazeous ammonia in CH2Cl2. Its has been later on transformed to the corresponding hydrobromide on reaction with 47% aqueous HBr solution for comparison purposes12f
  • Amstrong , M. D. 1948 . J. Amer. Chem. Soc. , 70 : 1756
  • [α]20D (a) = + 17.67°, c = 1, 1 N HCl, litt3 : + 18.6° under identical conditions (b) = − 16.14°, c = 1, H2O (c) = + 17.82°, c = 1, 1N HCl (d) = + 19.52°, c = 1, 1N HCl (e) = + 24.3°, c = 8, 6N HCl at 23°C8b (f) = − 20.24°, c = 1, H2O, Litt 11 -21° under similar conditions but at 27°C
  • Yamada , S. I. , Ninomiya , K. and Shioiri , T. 1973 . Tetrahedron Lett. , : 2343 and references cited
  • Boche , G. , Bernheim , M. and Schrott , W. 1982 . Tetrahedron Lett. , 23 : 5399
  • Hiyama , T. and Kai , M. 1982 . Tetrahedron Lett. , 23 : 2103
  • Schölkopf , U. , Harms , R. and Hoppe , D. 1973 . Liebigs Ann. Chem. , : 611

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