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Volumn 7, Issue 7, 2005, Pages 1423-1426

Highly efficient approach to orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYORNITHINE; ALDEHYDE; BETA LACTAM ANTIBIOTIC; BIPHENOMYCIN A; CLAVALANINE; COPPER COMPLEX; HOMOSERINE; NITROMETHANE; ORNITHINE DERIVATIVE; OXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 17444403980     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0503182     Document Type: Article
Times cited : (36)

References (52)
  • 23
    • 0043032892 scopus 로고    scopus 로고
    • For recent use of this versatile chiral building block, see: (a) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183. (b) Catalano, J. G.; Deaton, D. N.; Furfine, E. S.; Hassell, A. M.; McFayden, R. B.; Miller, A. B.; Miller, L. R.; Shewchuk, L. M.; Willard, D. H.; Whright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 275-278. (c) Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2004, 69, 5023-5036. (d) Dondoni, A.; Giovanni, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
    • (2003) J. Org. Chem. , vol.68 , pp. 6172-6183
    • Dondoni, A.1    Massi, A.2    Minghini, E.3    Sabbatini, S.4    Bertolasi, V.5
  • 25
    • 3543008950 scopus 로고    scopus 로고
    • For recent use of this versatile chiral building block, see: (a) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183. (b) Catalano, J. G.; Deaton, D. N.; Furfine, E. S.; Hassell, A. M.; McFayden, R. B.; Miller, A. B.; Miller, L. R.; Shewchuk, L. M.; Willard, D. H.; Whright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 275-278. (c) Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2004, 69, 5023-5036. (d) Dondoni, A.; Giovanni, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
    • (2004) J. Org. Chem. , vol.69 , pp. 5023-5036
    • Dondoni, A.1    Catozzi, N.2    Marra, A.3
  • 26
    • 4444268846 scopus 로고    scopus 로고
    • For recent use of this versatile chiral building block, see: (a) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183. (b) Catalano, J. G.; Deaton, D. N.; Furfine, E. S.; Hassell, A. M.; McFayden, R. B.; Miller, A. B.; Miller, L. R.; Shewchuk, L. M.; Willard, D. H.; Whright, L. L. Bioorg. Med. Chem. Lett. 2004, 14, 275-278. (c) Dondoni, A.; Catozzi, N.; Marra, A. J. Org. Chem. 2004, 69, 5023-5036. (d) Dondoni, A.; Giovanni, P. P.; Massi, A. Org. Lett. 2004, 6, 2929-2932.
    • (2004) Org. Lett. , vol.6 , pp. 2929-2932
    • Dondoni, A.1    Giovanni, P.P.2    Massi, A.3
  • 27
    • 17444383697 scopus 로고    scopus 로고
    • note
    • An analogous Henry reaction-based strategy for the synthesis of 4-hydroxyornithine was previously reported by Rudolph et al. (ref 9). This approach, however, suffers both from an unfavorable stereoselectivity and from a very low yield in the key nitroaldol reaction step and therefore was not pursued further.
  • 28
    • 17444384046 scopus 로고    scopus 로고
    • see Supporting Information
    • Although N-Boc-protected (5)-2-amino-1,4-butandiol 7 is commercially available (Aldrich), its relatively high price leads us to recommend its preparation on a multigram scale from inexpensive L-aspartic acid (see Supporting Information).
  • 32
    • 17444382583 scopus 로고    scopus 로고
    • note
    • Ab initio MO calculations (DFTYB3LYP/6-311G+) showed an energy difference of about 7.8 kcal/mol between 9 and the six-membered cyclic N,O-acetal 10, indicating that only traces of this regioisomer are to be expected.
  • 33
    • 17444411390 scopus 로고    scopus 로고
    • note
    • 2, rt, 36 h) according to ref 15.
  • 37
    • 17444364357 scopus 로고    scopus 로고
    • note
    • Low stereoselectivity in nitroaldol reactions with aldehydes bearing a stereogenic center at the β-position has been observed previously. See ref 9 and references therein.
  • 49
    • 17444402740 scopus 로고    scopus 로고
    • note
    • Since β-nitro alcohols 12 and 13 were difficult to separate, 12 was used as a mixture of diastereomers (97:3). The minor diastereomer could be easily removed by flash chromatography on silica gel at the stage of the N°-Z-protected β-amino alcohol 17.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.