Chirally Selective Synthesis of Sugar Moiety of Nucleosides by Chemicoenzymatic Approach: L- and D-Riboses, Showdomycin, and Cordycepin

Journal of the American Chemical Society

Volumn 103, Issue 22, 1981, Pages 6739-6741

  Ito, Yukishige ^a   Shibata, Tomoyuki ^a   Arita, Masafumi ^a   Sawai, Hiroaki ^a   Ohno, Masaji ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000199517     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00412a034     Document Type: Article

References (23)

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2. Ohno, M. “Anticancer Agents based on Natural Product Models”; Cassady, J. M.; Douros, J. D., Eds.; Academic Press: New York, 1980; pp 73-130.
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4. Just, G.; Liak, T. J.; Lim, M.-L.; Potvin, P.; Tsantrizos, Y. S. Can. J. Chem. 1980, 58, 2024 and references cited therein,
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6. Gensler, W. J.; Chau, S.; Ball, D. B. J. Am. Chem. Soc. 1975, 97, 436.
7. A chirally economic synthesis is characterized by recycling of the undesired isomer. See: (a) Kozikowski, A. P.; Floyd, W. C., Kuniak, M. P. J. Chem. Soc., Chem. Commun. 1977, 582.
8. Kozikowski, A. P.; Ames, A. J. Am. Chem. Soc. 1981, 103, 3923.
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13. Compound 2 was first used in the synthesis of C-nucleosides by Just et al. Just, G.; Martel, A. Tetrahedron Lett. 1973, 1517.
14. For compound 3, see: Zefirov, N. S.; Davydova, A. F.; Abdulvaleeva, F. A.; Yurev, Y. K. Zh. Obshck. Kim. 1966, 36, 197.
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20. For the cleavage to ribose, see: Levene, P. A.; Stiller, E. T. J. Biol. Chem. 1934, 102, 187.
21. For recent synthesis of 19, see: Inoue, T.; Kuwajima, I. J. Chem. Soc., Chem. Commun. 1980, 251 and references cited therein and ref 3b.
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23. The corresponding saturated meso compound derived from furan maleic anhydride was hydrolyzed very slowly with the esterase. For the Diels-Alder adduct, see: Daniels, R.; Fischer, J. L. J. Org. Chem. 1963, 28, 320.