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Volumn 19, Issue 22, 2008, Pages 2620-2631

Asymmetric synthesis of tetrahydrolipstatin and valilactone

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; TETRAHYDROLIPSTATIN; UNCLASSIFIED DRUG; VALILACTONE;

EID: 57149105510     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.11.012     Document Type: Article
Times cited : (28)

References (97)
  • 37
    • 0033972194 scopus 로고    scopus 로고
    • One further reference reports the synthesis of tetrahydrolipstatin 3; in this article a 1:1 mixture of diastereoisomers is obtained, although the details of their separation are not included. See:
    • One further reference reports the synthesis of tetrahydrolipstatin 3; in this article a 1:1 mixture of diastereoisomers is obtained, although the details of their separation are not included. See:. Parsons P.J., and Cowell J.K. Synlett (2000) 107
    • (2000) Synlett , pp. 107
    • Parsons, P.J.1    Cowell, J.K.2
  • 68
    • 0001278899 scopus 로고
    • The (R)-α-methylbenzylamine used for derivatisation was determined to be of 99% ee. An analogous reaction was also carried out using racemic β-lactone 13 producing a 50:50 mixture of diastereoisomeric amides, thus confirming that a resolution process was not occurring. For a related example, see:
    • The (R)-α-methylbenzylamine used for derivatisation was determined to be of 99% ee. An analogous reaction was also carried out using racemic β-lactone 13 producing a 50:50 mixture of diastereoisomeric amides, thus confirming that a resolution process was not occurring. For a related example, see:. Giresbeck A., and Seebach D. Helv. Chim. Acta 70 (1987) 1326
    • (1987) Helv. Chim. Acta , vol.70 , pp. 1326
    • Giresbeck, A.1    Seebach, D.2
  • 77
    • 57149090585 scopus 로고    scopus 로고
    • note
    • 4.
  • 83
    • 57149095330 scopus 로고    scopus 로고
    • note
    • 31P NMR spectroscopy which enabled a diastereoisomeric ratio of 96:3:1 to be determined.
  • 86
    • 57149105207 scopus 로고    scopus 로고
    • note
    • An authentic sample of tetrahydrolipstatin 3 was kindly supplied by Dr. M. Karpt and Dr. U. Zutter of Hoffman-La Roche.
  • 87
    • 57149097343 scopus 로고    scopus 로고
    • note
    • 4.
  • 89
    • 57149084759 scopus 로고    scopus 로고
    • note
    • 31P NMR spectroscopy; comparison with authentic samples of the minor diastereoisomers (and analogues produced during the synthesis of tetrahydrolipstatin 3) enabled a diastereoisomeric ratio of 93:5:2 to be determined.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.