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Nicolaou, K.C.1
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29444438131
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Hydrogen bonding in acyclic 1,3-diols may induce a solution conformation analogous to that of acetonide protecting groups
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Hydrogen bonding in acyclic 1,3-diols may induce a solution conformation analogous to that of acetonide protecting groups:, C. E. Anderson, D. K. Britt, S. Sangji, D. J. O'Leary, C. D. Anderson, S. D. Rychnovsky, Org. Lett. 2005, 7, 5721.
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30
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79951862747
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Note
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The use of sterically bulky cladinose and desosamine sugar residues at the C-3 and C-5 hydroxy groups were thought to reduce the conformational mobility along the C-1-C-8 subunit of the backbone and facilitate cyclization of erythromycinB precursors (Ref.[10b]). Given this, we anticipate the use of larger, more removable protecting groups than methyl ethers will not impede cyclizations.
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31
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79951875056
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Streamlining synthesis by late-stage Ci-H oxidation
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Streamlining synthesis by late-stage Ci-H oxidation
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32
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13444287979
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for the first explicit demonstration of this concept, see
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for the first explicit demonstration of this concept, see, K. J. Fraunhoffer, D. A. Bachovchin, M. C. White, Org. Lett. 2005, 7, 223
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Bachovchin, D.A.2
White, M.C.3
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Covell, D.J.1
Vermeulen, N.A.2
White, M.C.3
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35
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79951872822
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Ref.[6]
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Ref.[6]
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36
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77955564047
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for excellent reviews, see
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N. A. Vermeulen, J. H. Delcamp, M. C. White, J. Am. Chem. Soc. 2010, 132, 11323; for excellent reviews, see
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Vermeulen, N.A.1
Delcamp, J.H.2
White, M.C.3
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38
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84892323094
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Springer, Heidelberg,; for some elegant examples of late-stage Ci-H hydroxylation and amination, see
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R. W. Hoffmann, in Elements of Synthesis Planning, Springer, Heidelberg, 2009; for some elegant examples of late-stage Ci-H hydroxylation and amination, see
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(2009)
Elements of Synthesis Planning
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Hoffmann, R.W.1
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39
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12344263136
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P. A. Wender, M. K. Hilinski, A. V. W. Mayweg, Org. Lett. 2005, 7, 79
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Wender, P.A.1
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43
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79951898879
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For branched intermolecular allylic oxidations, see
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For branched intermolecular allylic oxidations, see
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45
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18744372130
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M. S. Chen, N. Prabagaran, N. A. Labenz, M. C. White, J. Am. Chem. Soc. 2005, 127, 6970
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Chen, M.S.1
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49
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0001616071
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Although in the original studies by Woodward etal. (Ref.[4]), acylation-based macrolactonization was effected by the Corey method (Ref.[2]), nearly all subsequent studies have used the Yamaguchi protocol (Refs.[5c,d,f-i, 6])
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Although in the original studies by Woodward etal. (Ref.[4]), acylation-based macrolactonization was effected by the Corey method (Ref.[2]), nearly all subsequent studies have used the Yamaguchi protocol (Refs.[5c,d,f-i, 6]);, J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989.
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Inanaga, J.1
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Saeki, H.3
Katsuki, T.4
Yamaguchi, M.5
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50
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79951893471
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Allylic alcohol 5 (Scheme3) gave a comparable macrolactonization yield to that of an analogous saturated alcohol under identical Yamaguchi conditions (namely, 87 % and 86 %, respectively, Ref.[5g])
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Allylic alcohol 5 (Scheme3) gave a comparable macrolactonization yield to that of an analogous saturated alcohol under identical Yamaguchi conditions (namely, 87 % and 86 %, respectively, Ref.[5g]).
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51
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79951925971
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Note
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It is clear that the polypropionate core of the erythromycins (6-dEB) does not require artificial preorganization for macrocyclization. While we cannot exclude the possibility that erythronolideB or A would require preorganization because of the presence of a C-6 and/or C-12 hydroxy group(s), the fact that linear precursors to erythronolideB, A, and 6-dEB have all been cyclized under comparable Yamaguchi conditions using the same cyclic biasing elements in the same positions, strongly suggests that they will continue to behave in a very similar manner to 6-dEB (see Ref.[5f,g,i]).
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