1,5-radical translocation protocol for the generation of C-1′ radicals in nucleosides. Synthesis of spiro nucleosides through a rare 5-endo-trig cyclization

Journal of Organic Chemistry

Volumn 61, Issue 6, 1996, Pages 1908-1909

  Gimisis, T ^a   Chatgilialoglu, C ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001057597     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952218n     Document Type: Article

References (25)

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2. For reviews, see: (a) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191-198 (b) Nicolau, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. (c) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769.
3. For reviews, see: (a) Goldberg, I. H. Acc. Chem. Res. 1991, 24, 191-198 (b) Nicolau, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. (c) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 746-769.
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20. There was ca. 80% deuterium incorporation on the C-8 position of (E)-3 and (Z)-3 but no measurable (<4%) deuterium incorporation in the anomeric C-1′ position of either compound. Furthermore, there was no deuterium incorporation observed in 7 or 8.
21. H2 fashion with ditin to regenerate the silyl or stannyl radicals, thus completing the cycle of these chain reactions.
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24. A recent synthetically useful application of a 5-endo-trig radical cyclization of N-vinylic-α,α-bis(phenylthio)acetamides bears a geometric resemblance to our system. Sato, T.; Nakamura, N.; Ikeda, K.; Okada, M.; Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1992, 2399-2407.
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