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Volumn 124, Issue 38, 2002, Pages 11368-11378

Enantioselective synthesis of the protein phosphatase inhibitor (-)-motuporin

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE FRAGMENTS;

EID: 0037174423     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0206700     Document Type: Article
Times cited : (59)

References (86)
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    • See ref 15 for detailed discussion
    • See ref 15 for detailed discussion.
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    • Preliminary communication on the synthesis of 3, see: Panek, J.; Hu, T. J. Org. Chem. 1997, 62, 4914-4915.
    • (1997) J. Org. Chem. , vol.62 , pp. 4914-4915
    • Panek, J.1    Hu, T.2
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    • note
    • 5 failed. Reaction under basic conditions with TBAF/THF was also carried out, but no reaction ensued.
  • 53
    • 0001174736 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K.
    • (c) Smith, K.; Pelter, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, p 703.
    • (1991) Comprehensive Organic Synthesis , vol.8 , pp. 703
    • Smith, K.1    Pelter, A.2
  • 65
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    • Our preliminary results of the hydrozirconation and subsequent cross-coupling strategy have been published. See: Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4912-4913.
    • (1997) J. Org. Chem. , vol.62 , pp. 4912-4913
    • Panek, J.S.1    Hu, T.2
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    • note
    • Compound 14 was prepare by DCC mediated coupling between commecially available N-Boc-(L)-Val and trimethylsilyl ethanol in the presence of catalytic amount of DMAP
  • 73
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    • note
    • Although other peptide coupling conditions were also attempted, similar levels of racemization were observed in this segment coupling reaction.
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    • Decreased reaction times resulted in isolation of mixtures of aldehyde and desired carboxylic acid. For a review, see: Ley, S.; Norman, J.; Griffith, W.; Marsden, S. Synthesis 1994, 639-666.
    • (1994) Synthesis , pp. 639-666
    • Ley, S.1    Norman, J.2    Griffith, W.3    Marsden, S.4
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    • note
    • 2/Pd-C/EtOH at room temperature for 15 h.
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    • note
    • 1H NMR (400 MHz) analysis on crude reaction mixtures.
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    • Ph.D. Thesis, Harvard University June
    • Robert J. Valentekovich, Ph.D. Thesis, Harvard University, June 1995.
    • (1995)
    • Valentekovich, R.J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.