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Volumn 75, Issue 15, 2010, Pages 5048-5064

An enantioselective convergent route to pamamycin 621A

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; ALDOL CONDENSATION; ALDOL REACTIONS; AZIDO GROUP; CHIRAL AUXILIARIES; CHIRAL BUILDING BLOCKS; ENANTIOSELECTIVE; LINEAR PRECURSORS; MAGNESIUM CHLORIDES; NATURAL ANTIBIOTICS; SIDE REACTIONS; STEREOGENIC CENTERS; TOTAL SYNTHESIS; TRIBUTYLTIN;

EID: 77955164504     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100774n     Document Type: Article
Times cited : (19)

References (101)
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    • 2 as the solvent led to extremely slow reaction at different concentrations with a large excess of the added base/silylating agent with or without DMAP. Replacement of the TBSCl with TBSOTf did not result in any improvement. In DMF, the reaction proceeded much faster, in general, but relatively high substrate concentration (ca. 1 M) is recommended
    • 2 as the solvent led to extremely slow reaction at different concentrations with a large excess of the added base/silylating agent with or without DMAP. Replacement of the TBSCl with TBSOTf did not result in any improvement. In DMF, the reaction proceeded much faster, in general, but relatively high substrate concentration (ca. 1 M) is recommended.
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    • 0034601959 scopus 로고    scopus 로고
    • For a practical high-yielding route to such auxiliaries, see
    • For a practical high-yielding route to such auxiliaries, see: Wu, Y.-K.; Shen, X. Tetrahedron: Asymmetry 2000, 11, 4359-4363
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 4359-4363
    • Wu, Y.-K.1    Shen, X.2
  • 77
    • 77955131975 scopus 로고    scopus 로고
    • For a convenient/practical synthesis of such auxiliaries, see
    • For a convenient/practical synthesis of such auxiliaries, see: Wu, Y.-K.; Yang, Y.-Q.; Hu, Q. J. Org. Chem. 2004, 69, 3390-3392
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    • Wu, Y.-K.1    Yang, Y.-Q.2    Hu, Q.3
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    • Elevated temperature or prolonged reaction time all resulted in undesired desilylation of 41a / 41b leading to 42a / 42b
    • Elevated temperature or prolonged reaction time all resulted in undesired desilylation of 41a / 41b leading to 42a / 42b.
  • 85
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    • Also compare many examples in:;;, For previous investigations on substrate-induced stereoselective reduction of propargyl ketones, see;;; Tetrahedron 2003, 59, 8613-8622
    • Also compare many examples in: Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100 For previous investigations on substrate-induced stereoselective reduction of propargyl ketones, see; Chakraborty, T. K.; Reddy, V. R.; Reddy, T. J. Tetrahedron 2003, 59, 8613-8622
    • (1990) Tetrahedron Lett. , vol.31 , pp. 7099-7100
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    • For a literature precedent of addition primary amine for similar purposes, see
    • For a literature precedent of addition primary amine for similar purposes, see: Czech, B. P.; Bartsch, R. A. J. Org. Chem. 1984, 49, 4076-4078
    • (1984) J. Org. Chem. , vol.49 , pp. 4076-4078
    • Czech, B.P.1    Bartsch, R.A.2
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    • 0035356401 scopus 로고    scopus 로고
    • Such reactions typically occur under basic conditions. For some examples (kindly provided by one of the reviewers) of related cyclization under acidic conditions, see
    • Such reactions typically occur under basic conditions. For some examples (kindly provided by one of the reviewers) of related cyclization under acidic conditions, see: Chakraborty, T. K.; Das, S.; Raju, T. V. J. Org. Chem. 2001, 66, 4091-4093
    • (2001) J. Org. Chem. , vol.66 , pp. 4091-4093
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    • For a recent review on stereoselective construction of THF rings, see:; Tetrahedron 2006, 63, 261-290
    • Dehmlow, H.; Multzer, J.; Seilz, C.; Strecker, A. R.; Kohlmann, A. Tetrahedron Lett. 1992, 33, 3607-3610 For a recent review on stereoselective construction of THF rings, see: Wolfe, J. P.; Hay, M. B. Tetrahedron 2006, 63, 261-290
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    • Dehmlow, H.1    Multzer, J.2    Seilz, C.3    Strecker, A.R.4    Kohlmann, A.5    Wolfe, J.P.6    Hay, M.B.7
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    • 3SnH reduction of azides, but they all required AIBN (2,2′-azobis(2-methylpropionitrile)) to initiate the reactions:;, and the refs cited therein
    • 3SnH reduction of azides, but they all required AIBN (2,2′-azobis(2-methylpropionitrile)) to initiate the reactions: Hays, D. S.; Fu, G. J. Org. Chem. 1998, 63, 2796-2797 and the refs cited therein.
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    • Those steps that are not given in this section were reported in the Supporting Information for ref 8
    • Those steps that are not given in this section were reported in the Supporting Information for ref 8.


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