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Volumn 73, Issue 9, 2008, Pages 3619-3622

Chiron approach to the synthesis of (2S,3R)-3-hydroxypipecolic acid and (2R,3R)-3-hydroxy-2-hydroxymethylpiperidine from D-glucose

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; OLEFINS; OXIDATION; REDUCTION;

EID: 43449084947     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702749r     Document Type: Article
Times cited : (44)

References (45)
  • 1
    • 77957037489 scopus 로고    scopus 로고
    • Pyridine and Piperidine Alkaloids: An Update
    • Pelletier, S. W, Ed, Pergamon: Oxford
    • (a) Schneider, M. J. Pyridine and Piperidine Alkaloids: An Update. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, p 155.
    • (1996) Alkaloids: Chemical and Biological Perspectives , vol.10 , pp. 155
    • Schneider, M.J.1
  • 8
    • 0035902404 scopus 로고    scopus 로고
    • For 2a and 2b, see: (a) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachib, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817.
    • For 2a and 2b, see: (a) Banba, Y.; Abe, C.; Nemoto, H.; Kato, A.; Adachib, I.; Takahata, H. Tetrahedron: Asymmetry 2001, 12, 817.
  • 16
    • 0033553450 scopus 로고    scopus 로고
    • For trans isomer 1b and its enantiomer, see: (a) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
    • For trans isomer 1b and its enantiomer, see: (a) Horikawa, M.; Busch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
  • 30
    • 28044433662 scopus 로고    scopus 로고
    • For 1a and 1b, see: (a) Liang, N.; Datta, A. J. Org. Chem. 2005, 70, 10182.
    • For 1a and 1b, see: (a) Liang, N.; Datta, A. J. Org. Chem. 2005, 70, 10182.
  • 32
    • 0027404924 scopus 로고    scopus 로고
    • For the enantiomer of 1a, see: (c) Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. Tetrahedron: Asymmetry 1993, 4, 625.
    • For the enantiomer of 1a, see: (c) Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. Tetrahedron: Asymmetry 1993, 4, 625.
  • 33
    • 0001387004 scopus 로고    scopus 로고
    • This paper does not describe the synthesis of the free amino acid but the protected version: N-t-BOC (2R,3S)-3- hydroxymethylpipecolate: (d) Roemmele, R. C, Rapoport, H. J. J. Org. Chem. 1989, 54, 1866
    • This paper does not describe the synthesis of the free amino acid but the protected version: N-t-BOC (2R,3S)-3- hydroxymethylpipecolate: (d) Roemmele, R. C.; Rapoport, H. J. J. Org. Chem. 1989, 54, 1866.
  • 34
    • 84970554509 scopus 로고    scopus 로고
    • For the enantiomer of 2b, see: (e) Mocerino, M.; Stick, R. V. Aust. J. Chem. 1990, 43, 1183.
    • For the enantiomer of 2b, see: (e) Mocerino, M.; Stick, R. V. Aust. J. Chem. 1990, 43, 1183.
  • 35
    • 84989580839 scopus 로고    scopus 로고
    • For the enantiomer of 2a, see: (f) Enders, D.; Jegelka, U. Synlett 1992, 999.
    • For the enantiomer of 2a, see: (f) Enders, D.; Jegelka, U. Synlett 1992, 999.
  • 36
    • 33748730715 scopus 로고    scopus 로고
    • Knight, D. W, Lewis, N, Share, A. C, Haigh, D. J. Chem. Soc, Perkin Trans. 1 1998, 3673. This paper does not describe the synthesis of the free amino piperidine diol but the protected version: N-t-BOC (2S,3S)-3-hydroxy-2-hydroxymethylpiperidine. Also see ref 8j
    • (g) Knight, D. W.; Lewis, N.; Share, A. C.; Haigh, D. J. Chem. Soc., Perkin Trans. 1 1998, 3673. This paper does not describe the synthesis of the free amino piperidine diol but the protected version: N-t-BOC (2S,3S)-3-hydroxy-2-hydroxymethylpiperidine. Also see ref 8j.
  • 44
    • 43449136027 scopus 로고    scopus 로고
    • Our attempts to separate the diastereomeric mixture of 6 by flash chromatography were unsuccessful due to the close Rf values; however, we have isolated the E-isomer in a small quantity, and its data are given in the Experimental Section. Compound 6 (E-isomer) is known; however, no data are reported to be the same. See: Chanderasekhar, S, Samala, J. P, Chennamaneni, L. R. J. Org. Chem. 2006, 71, 2196
    • f values; however, we have isolated the E-isomer in a small quantity, and its data are given in the Experimental Section. Compound 6 (E-isomer) is known; however, no data are reported to be the same. See: Chanderasekhar, S.; Samala, J. P.; Chennamaneni, L. R. J. Org. Chem. 2006, 71, 2196.
  • 45
    • 43449107819 scopus 로고    scopus 로고
    • Compound 7 is prepared by a different method in which the nature of the compound and specific rotation is not given; see ref 13. We have isolated compound 7 as a white solid and characterized it independently. The data are given in the Experimental Section
    • Compound 7 is prepared by a different method in which the nature of the compound and specific rotation is not given; see ref 13. We have isolated compound 7 as a white solid and characterized it independently. The data are given in the Experimental Section.


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