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Volumn 63, Issue 13, 1998, Pages 4489-4493

One-Pot Conversion of α,β-Unsaturated Alcohols into the Corresponding Carbon-Elongated Dienes with a Stable Phosphorus Ylide-BaMnO4 System. Synthesis of 6′-Methylene Derivatives of Neplanocin A as Potential Antiviral Nucleosides. New Neplanocin Analogues. 11

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; NEPLANOCIN A; NUCLEOSIDE DERIVATIVE;

EID: 0032568914     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971374m     Document Type: Article
Times cited : (55)

References (43)
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    • For examples of oxidation of allycil alcohols, see: (a) Ebenezer, W. J.; Wighy, P. In Comprehensive Organic Functional Group Trasformations; Katritzky, A. R., Methi-Cohn, O., Rees, C. W., Eds.; Pergamon Press: Oxford, 1995; Vol 3; pp 57 and 215. (b) Procter, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 305-325.
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    • 4, and PDC oxidations of 6 were tried, but no 7 was obtained.
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    • 4 is easy to handle and requires no activation, which makes it particulary useful for large-scale reactions; see: (a) Firouzabadi H.; Ghaderi, E. Tetrahedron Lett. 1978, 839-840. (b) Fatiadi, A. J. Synthesis 1987, 85-127. (c) Kim, K. S.; Chung, S.; Cho, I. H.; Hahn, C. S. Tetraherdon Lett. 1989, 30, 2559-2562.
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    • 4 is easy to handle and requires no activation, which makes it particulary useful for large-scale reactions; see: (a) Firouzabadi H.; Ghaderi, E. Tetrahedron Lett. 1978, 839-840. (b) Fatiadi, A. J. Synthesis 1987, 85-127. (c) Kim, K. S.; Chung, S.; Cho, I. H.; Hahn, C. S. Tetraherdon Lett. 1989, 30, 2559-2562.
    • (1987) Synthesis , pp. 85-127
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    • 4 is easy to handle and requires no activation, which makes it particulary useful for large-scale reactions; see: (a) Firouzabadi H.; Ghaderi, E. Tetrahedron Lett. 1978, 839-840. (b) Fatiadi, A. J. Synthesis 1987, 85-127. (c) Kim, K. S.; Chung, S.; Cho, I. H.; Hahn, C. S. Tetraherdon Lett. 1989, 30, 2559-2562.
    • (1989) Tetraherdon Lett , vol.30 , pp. 2559-2562
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    • note
    • 2-Et, no 10 was obtained.
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    • 2 is not efficient for all of the desired oxidation reactions (see ref 8a). Shioiri reported that CMD has a constant efficiency as an oxidant: (a) Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252-1255. (b) Matsubara, J.; Nakao, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 33, 4187-4190. (c) Shioiri, T.; Aoyama, T.; Hamada, Y. Wako Junyaku Jihou 1997, 65, 12-14.
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    • 2 is not efficient for all of the desired oxidation reactions (see ref 8a). Shioiri reported that CMD has a constant efficiency as an oxidant: (a) Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252-1255. (b) Matsubara, J.; Nakao, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 33, 4187-4190. (c) Shioiri, T.; Aoyama, T.; Hamada, Y. Wako Junyaku Jihou 1997, 65, 12-14.
    • (1992) Tetrahedron Lett , vol.33 , pp. 4187-4190
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  • 25
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    • 2 is not efficient for all of the desired oxidation reactions (see ref 8a). Shioiri reported that CMD has a constant efficiency as an oxidant: (a) Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252-1255. (b) Matsubara, J.; Nakao, K.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1992, 33, 4187-4190. (c) Shioiri, T.; Aoyama, T.; Hamada, Y. Wako Junyaku Jihou 1997, 65, 12-14.
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    • For example, Marko and co-workers obtained the corresponding aα,β-unsaturated aldehydes of cinnamyl alcohol, geraniol, nerol, and thiophene-2-methanol, which were also used as substrates in our study, by an novel ruthenium-catalyzed oxidation in 60-80% isolated yields, while they described the conversion yields as almost quantitative: Marko, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661-12662.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12661-12662
    • Marko, I.E.1    Giles, P.R.2    Tsukazaki, M.3    Chelle-Regnaut, I.4    Urch, C.J.5    Brown, S.M.6
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