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Volumn 62, Issue 7, 1997, Pages 2139-2143

Sulfoxide-mediated asymmetric synthesis of glycosidase inhibitor precursors

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDASE INHIBITOR; MANNOSTATIN A; OXAZOLIDINONE DERIVATIVE;

EID: 0031006867     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961774u     Document Type: Article
Times cited : (21)

References (58)
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    • (1995) J. Org. Chem. , vol.60 , pp. 3280
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  • 13
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    • For recent references of six-membered ring derivatives see: (a) Jung, M. E.; Choe, S. W. T. J. Org. Chem. 1995, 60, 3280. (b) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099.
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    • Hudlicky, T.1    Rouden, J.2    Luna, H.3    Allen, S.4
  • 29
    • 11944251609 scopus 로고
    • For an overview of our work see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Solladié, G.; Carreño, M. C. In Organosulphur Chemistry: Synthetic Aspects; Page, B. C. P., Ed.; Academic Press: London, 1995; p 1.
    • (1995) Chem. Rev. , vol.95 , pp. 1717
    • Carreño, M.C.1
  • 30
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    • Page, B. C. P., Ed.; Academic Press: London
    • For an overview of our work see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717. (b) Solladié, G.; Carreño, M. C. In Organosulphur Chemistry: Synthetic Aspects; Page, B. C. P., Ed.; Academic Press: London, 1995; p 1.
    • (1995) Organosulphur Chemistry: Synthetic Aspects , pp. 1
    • Solladié, G.1    Carreño, M.C.2
  • 40
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    • With regard to the regioselectivity of cyclopentenone deprotonation (α′ or γ) see: Liang Chen, Y.; Mariano, P. S.; Little, G. M. O'Brian, D.; Huesmann, P. L. J. Org. Chem. 1981, 46, 4643. Koreeda M.; Mislankar, S. G. J. Am. Chem. Soc. 1983, 105, 7203.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7203
    • Koreeda, M.1    Mislankar, S.G.2
  • 43
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    • note
    • The absolute configuration of 9a and 9b was established by comparison of their NMR data with those of 2-sulfinylcyclopentanones previously described; see ref 8b.
  • 44
    • 8244233890 scopus 로고    scopus 로고
    • note
    • 3 and confirmed in a further step by means of Mosher's esters of the hydroxy derivative 3.
  • 47
    • 8244252336 scopus 로고    scopus 로고
    • note
    • Chromatographic purification of the hydroxy sulfoxides 4 yielded 4-(p-tolylsulfinyl)-2-cyclopenten-1-one (12) (the corresponding thioether was derived from compound 10), as a result of the hydrolysis of the enol ether moiety and the dehydration of the carbinol. chemical equation presented.
  • 52
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    • See: (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125. (c) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 512
    • Dale, J.A.1    Mosher, H.S.2
  • 53
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    • Morrison, J. D., Ed.; Academic Press: New York
    • See: (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125. (c) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
    • (1983) Asymmetric Synthesis , vol.1 , pp. 125
    • Yamaguchi, S.1
  • 54
    • 0000328533 scopus 로고
    • See: (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512. (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125. (c) Chan, T. H.; Nwe, K. T. J. Org. Chem. 1992, 57, 6107.
    • (1992) J. Org. Chem. , vol.57 , pp. 6107
    • Chan, T.H.1    Nwe, K.T.2
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    • note
    • 2 failed to yield the corresponding sulfinylcarbamate.
  • 58
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    • note
    • The use of the readily available (R)-8 (see ref 15) would give access to (R,R)-2, which possesses the same stereochemistry as mannostatin.


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