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Volumn 9, Issue 17, 1999, Pages 2625-2628

Asymmetric synthesis of novel quaternary α-hydroxy-δ-lactam dipeptide surrogates

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTAM DERIVATIVE; LACTAM DERIVATIVE;

EID: 0033530116     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00448-5     Document Type: Article
Times cited : (22)

References (35)
  • 1
    • 0009680449 scopus 로고    scopus 로고
    • note
    • th birthday.
  • 18
    • 0009749323 scopus 로고    scopus 로고
    • note
    • All new compounds were characterized by full spectroscopic (NMR, low/high resolution MS) data. Yields refer to spectroscopically and chromatographically homogenous (≥95% by HPLC, TLC) materials.
  • 23
    • 0009679933 scopus 로고    scopus 로고
    • note
    • The e.e. values reported for the diol adducts 3a-c were determined by chiral HPLC using an analytical Chiracel AD column, eluting with an isopropanol, hexane 40-60% gradient, 0.5 mL/min flow rate. The assignment of absolute stereochemistry follows from application of the Sharpless pneumonic (ref 6a). Furthermore, 4b and 5b were elaborated into active thrombin inhibitors with α-(R)-hydroxy quaternary lactam stereochemistry, which is deemed essential for high potency due to optimal binding at S3 of the thrombin active site (cf. ref 1, 3, and 4).
  • 24
    • 84989500123 scopus 로고
    • "Fortified" AD-mix is prepared by increasing the catalyst and chiral ligand loading of commercial AD-mix: (a) Walsh, P. J.; Sharpless, K. B. Synlett. 1993, 605.
    • (1993) Synlett. , pp. 605
    • Walsh, P.J.1    Sharpless, K.B.2
  • 26
    • 0028007652 scopus 로고
    • For AD studies on exocyclic alkylidene lactones and related substrates to generate quaternary α-hydroxy lactone derivatives see: Curran, D. P.; Ko, S. B. J. Org. Chem. 1994, 59, 6139.
    • (1994) J. Org. Chem. , vol.59 , pp. 6139
    • Curran, D.P.1    Ko, S.B.2
  • 30
    • 0000975316 scopus 로고    scopus 로고
    • Rappoport, Z.; Apeloig, Y., Eds.; Wiley, Chichester. UK
    • (b) Chatgilialoglu, C.; Ferrerei, C.; Gimisis, T. in Chem. Org. Silicon Compd. Rappoport, Z.; Apeloig, Y., Eds.; Wiley, Chichester. UK, 1998; Vol. 2 (Pt.2), 1539.
    • (1998) Chem. Org. Silicon Compd. , vol.2 , Issue.PT.2 , pp. 1539
    • Chatgilialoglu, C.1    Ferrerei, C.2    Gimisis, T.3
  • 33
    • 0009750495 scopus 로고
    • Morrison, J. D., Ed.; Academic: New York, Ch. 2
    • (c) Heathcock, C. H. In Asymmetric Synthesis, Morrison, J. D., Ed.; Academic: New York, 1983; Vol. 2, Ch. 2.
    • (1983) Asymmetric Synthesis , vol.2
    • Heathcock, C.H.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.