Adenosine Nucleoside Analog Synthesis via Electrophilic Activation of Electron Rich Alkenes

References

• Niedballa , U. and Vorbruggen , H. 1974 . J. Org. Chem. , : 39 25, 3654
   Web of Science ®Google Scholar
• Chavis , C. , Dumont , F. , Wightman , R. , Ziegler , J. and Imbach , J. 1982 . J. Org. Chem. , 47 : 202
   Web of Science ®Google Scholar
• Kiss , J. and Dsouza , R. 1980 . J. Carbohydr. Nucleosides. Nucleotides. , 7 : 141
   Google Scholar
• Mikhailov , S. 1984 . Biorg. Chem. (USSR) , 10 : 940
   Google Scholar
• Kawakami , H. , Ebata , T. , Koseki , K. , Okano , K. , Matsumoto , K. and Matsushita , H. 1993 . Heterocycles , 36 : 12 2765
   Google Scholar
• El-Ladhdach , A. , Matheu , M. and Castillon , S. 1994 . Tetrahedron , 50 ( 42 ) : 12219 In this work phenylsulfenylchloride was added to a fural to give a trans beta chloro sulfide intermediate which was subsequently displaced via a Lewis acid catalyzed reaction. Here phenylselenenylchloride was added to glycals to give trans beta chloro selenides which were utilized in a subsequent acid catalyzed condensation with protected pyrimidines
   Web of Science ®Google Scholar
• Ueda , T. and Watanabe , S. 1985 . Chem. Pharm. Bull. , 33 ( 9 ) : 3689 Here glycosylation was achieved via Lewis acid catalyzed coupling of a glycal with pyrimidines. Presumably via a Lewis acid – alkene electrophilic complex
   Web of Science ®Google Scholar
• Kocovsky , P. and Pour , M. 1990 . J. Org. Chem. , 55 : 5580
   Web of Science ®Google Scholar
• Griffith , R. C. , Gentile , R. J. , Davidson , T. A. and Scott , F. L. 1979 . J. Org. Chem. , 44 ( 20 ) : 3580 – 3582 .
   Web of Science ®Google Scholar
• Hall , H. K. , Schaefer , J. P. and Spanggord , R. J. 1972 . J. Org. Chem. , 37 ( 20 ) : 3069 – 3075 .
   Web of Science ®Google Scholar
• Liotta , D. and Sim , G. 1978 . Tet. Lett. , 50 : 4977 – 4980 .
   Google Scholar
• In compound (4) the coupling constant of the pyranyl protons between C-2 and C-3 is 10.2 Hz which is indicative of a trans relationship. The corresponding coupling constant in compound (3) of the furanyl protons C-2 and C-3 is 6.3 Hz
   Google Scholar
• Reich , H. 1974 . J. Org. Chem. , 39 ( 3 ) : 428
   Web of Science ®Google Scholar
• Nicolau , K. , Claremon , D. , Barnette , W. and Seitz , S. 1979 . J. Amer. Chem. Soc. , 101 ( 13 ) : 3704
   Web of Science ®Google Scholar