Stereoselective Synthesis of Ribonucleoside 3′,5′-Cyclic Methyl(phenyl)phosphonates and Phosphonothioates

References

• Alberts , B. B. , Bray , D. , Lewis , J. , Raff , M. , Roberts , K. and Watson , J. D. 1989 . “ Molecular Biology of the Cell ” . 2nd ed. Vol. 2 , 41 – 86 . New York & London : Garland Publ., Inc. . chapter, See for instance
   Google Scholar
• Cashel , M. and Gallant , J. 1969 . Nature (London) , 221 : 838 – 841 .
   PubMed Web of Science ®Google Scholar
• Ross , P. , Weinhouse , H. , Aloni , Y. , Michaeli , D. , Weinberger-Ohana , P. , Mayer , R. , Braun , S. , De Vroom , E. , Van der Marel , G. A. , van Boom , J. H. and Benzimann , M. 1987 . Nature (London) , 325 : 279 – 281 .
   PubMed Web of Science ®Google Scholar
• Ross , P. , Mayer , R. , Weinhouse , H. , Amikam , D. , Huggirat , Y. , Benzimann , M. , de Vroom , E. , Fidder , A. , de Paus , P. , Sliedregt , L. A.J.M. , van der Marel , G. A. and van Boom , J. H. 1990 . J. Biol. Chem. , 265 : 18933 – 18943 .
   PubMed Web of Science ®Google Scholar
• Robinson , G. A. , Butcher , R. W. and Sutherland , E. W. 1971 . “ Cyclic AMP ” . New York : Academic Press .
   Google Scholar
• Konijn , T. M. , Van de Meene , J. G.C. , Bonner , J. T. and Barkley , D. S. 1967 . Proc. Natl. Acad. Sci. U.S.A. , 58 : 1152 – 1154 .
   PubMed Web of Science ®Google Scholar
• Van Haastert , P. J.M. 1983 . J. Biol. Chem. , 258 : 9643 – 9648 .
   PubMedGoogle Scholar
• Marugg , J. E. , De Vroom , E. , Van der Marel , G. A. and Van Boom , J. H. 1986 . Nucleic Acids Res. , 14 : 2171 – 2185 .
   PubMed Web of Science ®Google Scholar
• Roelen , H. C.P.F. , De Vroom , E. , Van der Marel , G. A. and Van Boom , J. H. 1988 . Nucleic Acids Res. , 16 : 7633 – 7645 .
   PubMed Web of Science ®Google Scholar
• Griffin , B. E. , Jarman , M. and Reese , C. B. 1968 . Tetrahedron , 24 : 639 – 662 .
   PubMed Web of Science ®Google Scholar
• Van Boom , J. H. , Burgers , P. M.J. , Verdegaal , C. H.M. and Wille , G. 1978 . Tetrahedron , 34 : 1999 – 2007 .
   Google Scholar
• Van Boom , J. H. and Wreesmann , C. T.J. 1984 . “ Oligonucleotide Synthesis: A Practical Approach ” . Edited by: Gait , M. J. 153- Oxford, , U.K. : IRL-Press .
   Google Scholar
• Ogilvie , K. K. , Nemer , M. J. , Hakimelahi , G. H. , Proba , Z. A. and Lucas , M. 1982 . Tetrahedron Lett. , 23 : 2615 – 2618 .
   Google Scholar
• Wang , A. H.-J. to be published
   Google Scholar
• It is of interest to note that the stereoselective outcome of the two-step cyclisation process is independent from the chirality of the 2′-O-THP protecting group. For example, the two-step conversion of 10, (lrd) with either 2, or 6, gave exclusively the corresponding Sp-diastereoisomers 17, and 25.
   Google Scholar
• KÖnig , W. and Geiger , R. 1970 . Chem. Ber. , 103 : 788 – 798 .
   PubMedGoogle Scholar