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Xu, R.7
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33846495712
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33846509947
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Angew. Chem. Int. Ed. 2007, 46, 541-544.
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33846509387
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Our attempts to further optimize the Kocienski-Julia olefination were unsuccessful. In our model studies, the use of LiHMDS eliminates the side product, but decreases the E/Z ratio of the Δ12-olefin isomers to 2:1. Protection of the C15 alcohol as a triisopropylsilyl ether significantly diminishes the reactivity of the aldehyde because of steric hindrance
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12-olefin isomers to 2:1. Protection of the C15 alcohol as a triisopropylsilyl ether significantly diminishes the reactivity of the aldehyde because of steric hindrance.
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9
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0041790924
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a) I. Paterson, K. R. Gibson, R. M. Oballa, Tetrahedron Lett. 1996, 37, 8585-8588;
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Paterson, I.1
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0000271703
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Evans, D.A.1
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15844376790
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a) D. A. Evans, M. J. Dart, J. L. Duffy, J. Am. Chem. Soc. 1996, 118, 4322-4343;
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Evans, D.A.1
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b) D. A. Evans, J. L. Duffy, M. J. Dart, Tetrahedron Lett. 1994, 35, 8537-8540.
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Evans, D.A.1
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a) D. A. Evans, B. Côté, P. J. Coleman, B. T. Connell, J. Am. Chem. Soc. 2003, 125, 10 893-10 898;
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Evans, D.A.1
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28744431819
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b) L. C. Dias, A.M. Aguilar, A. G. Salles, L. J. Steil, W. R. Roush, J. Org. Chem. 2005, 70, 10 461-10 465.
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15
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33846536371
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D. A. Evans, P. Nagorny, unpublished results. Also see Ref. [7a] for precedent for this coupling.
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D. A. Evans, P. Nagorny, unpublished results. Also see Ref. [7a] for precedent for this coupling.
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16
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33947085552
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The stereochemistry of the C29 stereocenter was proven by the Mosher ester analysis. See: J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
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The stereochemistry of the C29 stereocenter was proven by the Mosher ester analysis. See: J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519.
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17
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33751386227
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E. Kim, D. M. Gordon, W. Schmid, G. M. Whitesides, J. Org. Chem. 1993, 58, 5500-5507.
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Kim, E.1
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18
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33846543359
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The inseparable impurity (ca. 9%) that arose from the Wacker oxidation of 3a and that was present in the ketone 8 starting material obscured the precise determination of the reaction diastereoselectivity with the lower limit of detection set at 10:1.
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The inseparable impurity (ca. 9%) that arose from the Wacker oxidation of 3a and that was present in the ketone 8 starting material obscured the precise determination of the reaction diastereoselectivity with the lower limit of detection set at 10:1.
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19
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0025058974
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13C NMR shift of the acetonide moiety. See:a S. D. Rychnovsky, D. J. Skalitzky, Tetrahedron Lett. 1990, 31, 945-948;
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13C NMR shift of the acetonide moiety. See:a) S. D. Rychnovsky, D. J. Skalitzky, Tetrahedron Lett. 1990, 31, 945-948;
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20
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33846497491
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b) S. D. Rychnovsky, B. Rogers, G. Yang, Tetrahedron Lett. 1990, 31, 3511-3515;
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c) D. A. Evans, D. L. Rieger, J. R. Gage, Tetrahedron Lett. 1990, 31, 7099-7100.
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0001616071
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J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
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a) M. Hikota, H. Tone, K. Horita, O. Yonemitsu, J. Org. Chem. 1990, 55, 7-9;
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0037078348
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26
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33846546684
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For further details, see the Supporting Information
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For further details, see the Supporting Information.
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27
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33846515358
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We found the optimal concentration of HF for the deprotection was 1-2 M, at 7°C as more concentrated solutions of HF or higher temperatures decompose oasomycin A. Minor amounts of mono-TBS-protected oasomycin A (ca. 10-20%) were also recovered after workup and then recycled. The yield reported was calculated after one such recycling.
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We found the optimal concentration of HF for the deprotection was 1-2 M, at 7°C as more concentrated solutions of HF or higher temperatures decompose oasomycin A. Minor amounts of mono-TBS-protected oasomycin A (ca. 10-20%) were also recovered after workup and then recycled. The yield reported was calculated after one such recycling.
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28
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33846493733
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We thank Professor Y. Kishi for providing the natural samples of oasomycin A and B
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We thank Professor Y. Kishi for providing the natural samples of oasomycin A and B.
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29
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84986720823
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0035819982
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and references therein
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