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Volumn 9, Issue 21, 2007, Pages 4211-4214

Stereoselective syntheses of 4-oxa diaminopimelic acid and its protected derivatives via aziridine ring opening

Author keywords

[No Author keywords available]

Indexed keywords

4 OXA 2,6 DIAMINOPIMELIC ACID; 4-OXA-2,6-DIAMINOPIMELIC ACID; ALANINE; AMINO ACID; AZIRIDINE; AZIRIDINE DERIVATIVE; DIAMINOPIMELIC ACID; DRUG DERIVATIVE; ISOMERASE; LANTHIONINE; SERINE; SULFIDE; THREONINE; UNCLASSIFIED DRUG;

EID: 35548992012     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701742x     Document Type: Article
Times cited : (40)

References (32)
  • 1
    • 33847633444 scopus 로고    scopus 로고
    • and references cited therein. For recent reviews, see: a
    • For recent reviews, see: (a) Vederas, J. C. Can. J. Chem. 2006, 84, 1197-1207 and references cited therein.
    • (2006) Can. J. Chem , vol.84 , pp. 1197-1207
    • Vederas, J.C.1
  • 10
    • 35548982032 scopus 로고
    • For synthesis of a mixture of oxa-DAP isomers, see
    • For synthesis of a mixture of oxa-DAP isomers, see: Zahn, H.; Dietrich, R.; Gerstner, W. Chem. Ber. 1955, 88, 1734-1746.
    • (1955) Chem. Ber , vol.88 , pp. 1734-1746
    • Zahn, H.1    Dietrich, R.2    Gerstner, W.3
  • 14
    • 1542375289 scopus 로고    scopus 로고
    • and references cited therein. For reviews, see: a
    • For reviews, see: (a) Hu, X. E. Tetrahedron 2004, 60, 2701-2743 and references cited therein.
    • (2004) Tetrahedron , vol.60 , pp. 2701-2743
    • Hu, X.E.1
  • 21
    • 0026056895 scopus 로고    scopus 로고
    • Enhanced nucleophilicity of the hydroxyl groups via intramolecular H-bonding has been offered as an explanation for glycosidation of serine and threonine, a Szabo, L, Li, Y, Polt, R. Tetrahedron Lett. 1991, 5, 585-588
    • Enhanced nucleophilicity of the hydroxyl groups via intramolecular H-bonding has been offered as an explanation for glycosidation of serine and threonine, (a) Szabo, L.; Li, Y.; Polt, R. Tetrahedron Lett. 1991, 5, 585-588.
  • 23
    • 35548990002 scopus 로고    scopus 로고
    • Bose, A. K. Organic Syntheses; Wiley & Sons: New York, 1973; Collect. V, pp 973-974.
    • Bose, A. K. Organic Syntheses; Wiley & Sons: New York, 1973; Collect. Vol. V, pp 973-974.
  • 24
    • 0033609784 scopus 로고    scopus 로고
    • A side product was isolated in 6% yield resulting from the attack of OH on the pNZ to form a benzyl ether. For such a side reaction, see: Osterkamp, F.; Wehlan, H.; Koert, U.; Wiesner, M.; Raddatz, P.; Goodman, S. Tetrahedron 1999, 55, 10713-10734.
    • A side product was isolated in 6% yield resulting from the attack of OH on the pNZ to form a benzyl ether. For such a side reaction, see: Osterkamp, F.; Wehlan, H.; Koert, U.; Wiesner, M.; Raddatz, P.; Goodman, S. Tetrahedron 1999, 55, 10713-10734.
  • 25
    • 0001009177 scopus 로고    scopus 로고
    • Intramolecular aziridine rearrangement with formation of oxazoline (5%) was observed during the synthesis of 6e. For rearrangement of acylaziridines to oxazolines using Lewis acids, see: (a) Ferraris, D.; Druey, W. J., III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568-4569.
    • Intramolecular aziridine rearrangement with formation of oxazoline (5%) was observed during the synthesis of 6e. For rearrangement of acylaziridines to oxazolines using Lewis acids, see: (a) Ferraris, D.; Druey, W. J., III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568-4569.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.