A stereoselective and efficient route to (3S, 4R, 5S)-(+)-4,5- dihydroxycyclopent-1-en-3-ylamine: The side chain of the hypermodified nucleoside Q

Tetrahedron Letters

Volumn 39, Issue 43, 1998, Pages 7987-7990

  Ovaa, Huib ^a   Codée, Jeroen D C ^a   Lastdrager, Bas ^a   Overkleeft, Herman S ^a   Van Der Marel, Gijsbert A ^a   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

galactosylation; Overman rearrangement; Queuosine; Ring closing metathesis

Indexed keywords

ALKADIENE; CYCLOPENTENE DERIVATIVE; FURAN DERIVATIVE; GALACTOSE; MANNOSE; QUEUOSINE;

ARTICLE; CHEMICAL MODIFICATION; GLYCOSYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032558611     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01738-9     Document Type: Article

References (18)

1. (1) Goodman, H. M.; Abelson, J.; Landy, A.; Brenner, S.; Smith, J. D. Nature 1968, 217, 1019.
2. (2) Ohgi, T.; Kondo, T.; Goto, T. J. Am. Chem. Soc. 1979, 101, 3629.
3. (3) Harada, F.; Nishimura, S. Biochemistry 1972, 11, 301.
4. (4) Kasai, H.; Kuchino, Y.; Nihei, K.; Nishimura, S. Nucleic Acids Res. 1975, 2, 1931.
5. (5) Kasai, H.; Nishimura, K.; MacFarlane, R. D.; Torgerson, D. F.; Ohashi, Z.; McCloskey, T. A.; Gross, H. J.; Nishimura, S. J. Am. Chem. Soc. 1976, 98, 5044.
6. (6) Kondo, T.; Okamoto, K.; Ohgi, T.; Goto, T. Tetrahedron 1986, 42, 207.
7. (7) (a) Tanaka, K.; Ogasawara, K. Synthesis 1996, 219.
8. (b) Ohgi, T.; Goto, T. Tetrahedron Lett. 1976, 33, 367.
9. (8) Ovaa, H.; Leeuwenburgh, M. A.; Overkleeft, H. S.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 1998, 39, 3025.
10. (9) Ohrui, H.; Emoto, S. Tetrahedron Lett. 1975, 32, 2765.
11. (10) Josan, J. S.; Eastwood, F. W. Jr. Carbohydr. Res. 1972, 24, 192.
12. (11) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
13. + 3:3:1.
14. (13) Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
15. (14) Brewster, H. J. Am. Chem. Soc. 1959, 81, 5493.
16. (15) Schmidt, R. R. Angew. Chem. Int. Ed. Engl. 1986, 25, 212.
17. Tyr of E. coli MRE 600.
18. Tyr of E. coli MRE 600.