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1
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a) A. Zampella, M. V. D'Auria, L. Minale, C. Debitus, C. Roussakis, J. Am. Chem. Soc. 1996, 118, 11085;
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Zampella, A.1
D'Auria, M.V.2
Minale, L.3
Debitus, C.4
Roussakis, C.5
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2
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0031550829
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b) A. Zampella, M. V. D'Auria, L. Minale, Tetrahedron 1997, 53, 3243.
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Tetrahedron
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Zampella, A.1
D'Auria, M.V.2
Minale, L.3
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3
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0037019541
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a) B. M. Trost, J. L. Gunzner, O. Dirat, Y. H. Rhee, J. Am. Chem. Soc. 2002, 124, 10396;
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Trost, B.M.1
Gunzner, J.L.2
Dirat, O.3
Rhee, Y.H.4
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4
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0012566571
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b) B. M. Trost, O. Dirat, J. L. Gunzner, Angew. Chem. 2002, 114, 869;
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Angew. Chem
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Trost, B.M.1
Dirat, O.2
Gunzner, J.L.3
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7
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0037157166
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a) D. A. Evans, E. Hu, J. D. Burch, G. Jaeschke, J. Am. Chem. Soc. 2002, 124, 5654;
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Evans, D.A.1
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Jaeschke, G.4
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8
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0035807581
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Evans, D.A.1
Hu, E.2
Tedrow, J.S.3
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10
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0344496723
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a) I. Paterson, R. D. M. Davies, A. C. Heimann, R. Marquez, A. Meyer, Org. Lett. 2003, 5, 4477;
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Org. Lett
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Paterson, I.1
Davies, R.D.M.2
Heimann, A.C.3
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Meyer, A.5
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11
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0012570716
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b) I. Paterson, R. D. M. Davies, R. Marquez, Angew. Chem. 2001, 113, 623;
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Angew. Chem
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Paterson, I.1
Davies, R.D.M.2
Marquez, R.3
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16
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0041733541
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a) S. P. Brown, M. P. Brochu, C. J. Sinz, D. W. C. MacMillan, J. Am. Chem. Soc. 2003, 125, 10808;
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Brown, S.P.1
Brochu, M.P.2
Sinz, C.J.3
MacMillan, D.W.C.4
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19
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9144264805
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a) A. B. Northrup, I. K. Mangion, F. Hettche, D. W. C. MacMillan, Angew. Chem. 2004, 116, 2204;
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Northrup, A.B.1
Mangion, I.K.2
Hettche, F.3
MacMillan, D.W.C.4
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22
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0030025692
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Stereochemistry has been previously established: K. Horita, T. Inoue, K. Tanaka, O. Yonemitsu, Tetrahedron 1996, 52, 531.
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Stereochemistry has been previously established: K. Horita, T. Inoue, K. Tanaka, O. Yonemitsu, Tetrahedron 1996, 52, 531.
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23
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53549110947
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D-proline catalysis: 12:1 anti/syn
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With D-proline catalysis: 12:1 anti/syn, 1:2 Felkin/anti-Felkin.
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2 Felkin/anti-Felkin
, vol.1
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With1
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24
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84950086559
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a) M. F. Semmelhack, C. Kim, N. Zhang, C. Bodurow, M. Sanner, W. Dobler, M. Meier, Pure Appl. Chem. 1990, 62, 2035;
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Semmelhack, M.F.1
Kim, C.2
Zhang, N.3
Bodurow, C.4
Sanner, M.5
Dobler, W.6
Meier, M.7
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27
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33845377563
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E. Negishi, D. E. Van Horn, T. Yoshida, J. Am. Chem. Soc. 1985, 107, 6639.
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J. Am. Chem. Soc
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Negishi, E.1
Van Horn, D.E.2
Yoshida, T.3
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28
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33847089947
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a) Y. Okude, S. Hirano, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 3179;
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J. Am. Chem. Soc
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Okude, Y.1
Hirano, S.2
Hiyama, T.3
Nozaki, H.4
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29
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33845375686
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b) H. Jin, J. Uenishi, W. J. Christ, Y. Kishi, J. Am. Chem. Soc. 1986, 108, 5644.
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J. Am. Chem. Soc
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Jin, H.1
Uenishi, J.2
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Kishi, Y.4
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0005732938
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J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989.
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Inanaga, J.1
Hirata, K.2
Saeki, H.3
Katsuki, T.4
Yamaguchi, M.5
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31
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0035932078
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The side chain was synthesized according to the procedure of Evans: D. A. Evans, J. D. Burch, Org. Lett. 2001, 3, 503.
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The side chain was synthesized according to the procedure of Evans: D. A. Evans, J. D. Burch, Org. Lett. 2001, 3, 503.
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32
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53549088466
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The HWE coupling was less effective when performed after the macrocyclization step (84% vs. 54% yield).
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The HWE coupling was less effective when performed after the macrocyclization step (84% vs. 54% yield).
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33
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34247112862
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K. C. Skepper, J. B. MacMillan, G. Zhou, M. M. Masuno, T. F. Molinski, J. Am. Chem. Soc. 2007, 129, 4150.
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J. Am. Chem. Soc
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Skepper, K.C.1
MacMillan, J.B.2
Zhou, G.3
Masuno, M.M.4
Molinski, T.F.5
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35
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0001183739
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a) L. F. Tietze, R. Fischer, H. J. Guder, A. Goerlach, M. Meumann, T. Krach, Carbohydr. Res. 1987, 164, 177;
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Carbohydr. Res
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Tietze, L.F.1
Fischer, R.2
Guder, H.J.3
Goerlach, A.4
Meumann, M.5
Krach, T.6
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37
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53549132674
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The macrolide 1 was formed as a 4:1 mixture of diastereomers at the anomeric position. Spectral data for each anomer was inconsistent with the characterization data for the natural isolate.
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The macrolide 1 was formed as a 4:1 mixture of diastereomers at the anomeric position. Spectral data for each anomer was inconsistent with the characterization data for the natural isolate.
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38
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53549083385
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We thank Professor L. Minale and co-workers for the Herculean taskof isolating and characterizing callipeltosides A-C. We thank Professor M. Valeria D'Auria for providing comparison spectra of natural 23 to D.W.C.M
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We thank Professor L. Minale and co-workers for the Herculean taskof isolating and characterizing callipeltosides A-C. We thank Professor M. Valeria D'Auria for providing comparison spectra of natural 23 to D.W.C.M.
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39
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53549083094
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At the present time we cannot state definitively the stereochemistry of the C1′ anomeric position of callipeltoside C. Based on the isolation studies for callipeltoside B, we tentatively suggest that it exists as the β-equatorial anomer as shown in Scheme 5
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At the present time we cannot state definitively the stereochemistry of the C1′ anomeric position of callipeltoside C. Based on the isolation studies for callipeltoside B, we tentatively suggest that it exists as the β-equatorial anomer as shown in Scheme 5.
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40
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53549130851
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We anticipate that the structure of callipeltoside B will likely be revised with respect to the enantiomer series of the pendent deoxyamino carbohydrate
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We anticipate that the structure of callipeltoside B will likely be revised with respect to the enantiomer series of the pendent deoxyamino carbohydrate.
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41
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53549101509
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The longest linear sequence is 18 steps and 12% overall yield from the Roche ester-derived aldehyde 6.
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The longest linear sequence is 18 steps and 12% overall yield from the Roche ester-derived aldehyde 6.
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42
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34250684250
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For a review on the organocatalytic synthesis of bioactive molecules
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For a review on the organocatalytic synthesis of bioactive molecules: R. M. F. Figueirido, M. Christmann, Eur. J. Org. Chem. 2007, 2575.
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(2007)
Eur. J. Org. Chem
, pp. 2575
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Figueirido, R.M.F.1
Christmann, M.2
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