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Volumn 70, Issue 5, 2005, Pages 1949-1952

Synthesis of a β-amino acid pharmacophore via a β-lactam intermediate

Author keywords

[No Author keywords available]

Indexed keywords

DRUG PRODUCTS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 14544301880     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048249c     Document Type: Article
Times cited : (27)

References (43)
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    • For reviews, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 23, 117. (c) Juaristi, E., Ed.; Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997. Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983-1004. (d) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
    • (1997) Enantioselective Synthesis of β-Amino Acids
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    • For reviews, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 23, 117. (c) Juaristi, E., Ed.; Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997. Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983-1004. (d) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
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    • Juaristi, E.1    Lopez-Ruiz, H.2
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    • For reviews, see: (a) Cole, D. C. Tetrahedron 1994, 50, 9517. (b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 23, 117. (c) Juaristi, E., Ed.; Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1997. Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983-1004. (d) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991.
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  • 9
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    • note
    • See ref 1d and references therein for most recent applications.
  • 20
    • 14544301507 scopus 로고    scopus 로고
    • note
    • 3) for 4: 3.62 (dt, J 19.4, 3.8, 1H), 3.86 (dt, J 3.8, 19.4, 1H), 5.01 (m, 1H), 7.17 (m, 1H), 7.29 (m, 1H), 7.47 (d, J 8.1, NH), 7.59 (m, 1H).
  • 24
    • 14544268640 scopus 로고    scopus 로고
    • note
    • 3) for 9: 3.29 (dd, J 1.4, 7.1, 2H), 3.74 (s, 3H), 6.38 (dt, J 7.1, 16, 1H), 6.59 (m, 1H), 6-86-7.04 (m, 2H), 7.15 (m, 1H).
  • 32
    • 0037427991 scopus 로고    scopus 로고
    • (g) Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 35-42. See also: Yang, H. W.; Romo, D. J. Org. Chem. 1999, 64, 7657-7660.
    • (2003) J. Org. Chem. , vol.68 , pp. 35-42
    • Durham, T.B.1    Miller, M.J.2
  • 33
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    • (g) Durham, T. B.; Miller, M. J. J. Org. Chem. 2003, 68, 35-42. See also: Yang, H. W.; Romo, D. J. Org. Chem. 1999, 64, 7657-7660.
    • (1999) J. Org. Chem. , vol.64 , pp. 7657-7660
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  • 35
    • 14544285552 scopus 로고    scopus 로고
    • note
    • Known examples required two- to four-step deprotection/protection for opening. See ref 14g.
  • 37
    • 14544278462 scopus 로고    scopus 로고
    • note
    • Use of triethylamine or pyridine led to the formation of bisacylated byproduct up to 15%.
  • 41
    • 14544274213 scopus 로고    scopus 로고
    • note
    • The ee is increased from 92 to >99.5% during crystallization in MeOH.
  • 42
    • 14544282028 scopus 로고    scopus 로고
    • note
    • Similarly, treatment of β-lactam 16 with LiOH in THF/water give the corresponding β-amino acid.
  • 43
    • 14544273311 scopus 로고    scopus 로고
    • note
    • When the hydrogenation is performed on the β-lactam 16, the NO-Bn bond is cleaved instead of the N-OBn bond, giving the N-hydroxyl β-lactam.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.