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Volumn 129, Issue 19, 2007, Pages 6336-6342

Concise, asymmetric, stereocontrolled total synthesis of stephacidins A, B and notoamide B

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; ESTERS; FUNCTIONAL GROUPS; FUNGI; METABOLITES; MICROWAVE HEATING; SYNTHESIS (CHEMICAL);

EID: 34249112804     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja070259i     Document Type: Article
Times cited : (139)

References (48)
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    • For a short review concerning the proposed mechanism of dimerization, see: Nussbaum, F. Angew. Chem., Int. Ed. 2003, 42, 2068-3071.
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    • Fenical, W.; Jensen, P.; Cheng, X. C. U.S. Patent 6,066,635, 2000; Chem. Abstr. 2000, 132, 346709.
    • Fenical, W.; Jensen, P.; Cheng, X. C. U.S. Patent 6,066,635, 2000; Chem. Abstr. 2000, 132, 346709.
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    • For a preliminary account of Myers' work, see
    • For a preliminary account of Myers' work, see: Myers, A. G.; Herzon, S. B. J. Am. Chem. Soc. 2003, 125, 12080-12081.
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    • Myers, A.G.1    Herzon, S.B.2
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    • For a full account of experiments conducted by the Baran, laboratories towards these alkaloids, see
    • For a full account of experiments conducted by the Baran, laboratories towards these alkaloids, see: Baran, P. S.; Hafensteiner, B. D.; Ambhaikar, N. B.; Guerrero, C. A.; Gallagher, J. D. J. Am. Chem. Soc. 2006, 128, 8678-8693.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 8678-8693
    • Baran, P.S.1    Hafensteiner, B.D.2    Ambhaikar, N.B.3    Guerrero, C.A.4    Gallagher, J.D.5
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    • For reviews of our previous synthetic and biosynthetic work concerning this class of alkaloids, see: a
    • For reviews of our previous synthetic and biosynthetic work concerning this class of alkaloids, see: (a) Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127-139.
    • (2003) Acc. Chem. Res , vol.36 , pp. 127-139
    • Williams, R.M.1    Cox, R.J.2
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    • For recent biomimetic total syntheses of notoamides B, C, D and stephacidin A from our laboratory, see: a
    • For recent biomimetic total syntheses of notoamides B, C, D and stephacidin A from our laboratory, see: (a) Grubbs, A. W.; Artman, G. D.; Tsukamoto, T.; Williams, R. M. Angew. Chem., Int. Ed. 2006, 46, 2257-2261.
    • (2006) Angew. Chem., Int. Ed , vol.46 , pp. 2257-2261
    • Grubbs, A.W.1    Artman, G.D.2    Tsukamoto, T.3    Williams, R.M.4
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    • Ph.D. Dissertation, University of Göttingen
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    • For preliminary studies towards the synthesis of the stephacidins using a biomimetic approach, see
    • For preliminary studies towards the synthesis of the stephacidins using a biomimetic approach, see: Adams, L. A.; Gray, C. R.; Williams, R. M. Tetrahedron Lett. 2004, 45, 4489-4493.
    • (2004) Tetrahedron Lett , vol.45 , pp. 4489-4493
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    • For reviews concerning microwave-assisted organic synthesis, see: a
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    • The thermal lability of the N-t-Boc protecting group has documented, see: Krakowiak, K. E.; Bradshaw, J. S. Synth. Commun. 1996, 26, 3999-4004.
    • (d) The thermal lability of the N-t-Boc protecting group has documented, see: Krakowiak, K. E.; Bradshaw, J. S. Synth. Commun. 1996, 26, 3999-4004.
  • 40
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    • For recent total syntheses that employ olefin cross-metathesis, see: a
    • For recent total syntheses that employ olefin cross-metathesis, see: (a) Trost, B. M.; Thiel, O. R.; Tsui, H.-C. J. Am. Chem. Soc. 2003, 125, 13155-13164.
    • (2003) J. Am. Chem. Soc , vol.125 , pp. 13155-13164
    • Trost, B.M.1    Thiel, O.R.2    Tsui, H.-C.3
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    • For microwave olefin cross-metathesis, see
    • For microwave olefin cross-metathesis, see: Bargiggia, F. C.; Murray, W. V. J. Org. Chem. 2005, 70, 9636-9639.
    • (2005) J. Org. Chem , vol.70 , pp. 9636-9639
    • Bargiggia, F.C.1    Murray, W.V.2
  • 45
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    • Similar results were observed by the Baran group during their synthetic efforts towards stephacidin A. Please see their full account listed in ref 8 for exact conditions explored
    • Similar results were observed by the Baran group during their synthetic efforts towards stephacidin A. Please see their full account listed in ref 8 for exact conditions explored.
  • 46
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    • Note added in revision: (a) For a biomimetic synthesis of the related alkaloid d,l-marcfotine C, see: Greshock, T. J.; Grubbs, A. W.; Williams, R. M. Tetrahedron 2007, DOI: 10.1016/j.tet.2007.03.016.
    • Note added in revision: (a) For a biomimetic synthesis of the related alkaloid d,l-marcfotine C, see: Greshock, T. J.; Grubbs, A. W.; Williams, R. M. Tetrahedron 2007, DOI: 10.1016/j.tet.2007.03.016.
  • 47
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    • For a recent synthesis of d,l-marcfortine B. see: Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086-3087.
    • (b) For a recent synthesis of d,l-marcfortine B. see: Trost, B. M.; Cramer, N.; Bernsmann, H. J. Am. Chem. Soc. 2007, 129, 3086-3087.
  • 48
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    • Note added in proof: Myers, et al., recently reported that stephacidin B converts to avrainvillamide in cell culture with avrainvillamide being the biologically active species: Wulff, J. E.; Herzon, S. B.; Siegrist, R.; Myers, A. G. J. Am. Chem. Soc. 2007, 129, 4898-4899.
    • Note added in proof: Myers, et al., recently reported that stephacidin B converts to avrainvillamide in cell culture with avrainvillamide being the biologically active species: Wulff, J. E.; Herzon, S. B.; Siegrist, R.; Myers, A. G. J. Am. Chem. Soc. 2007, 129, 4898-4899.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.