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9
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75749098379
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The natural product numbering
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The natural product numbering.
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10
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2342512851
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13
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0001780886
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Katsuki, T.1
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16
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0025811256
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2. For the preparation of achiral phosphonate 13, see: R. K. Boeckmann, Jr., T. M. Kmenecka, S. G. Nelson, J. R. Pruitt, T. E. Barta, Tetrahedron Lett. 1991, 32, 2581-2584.
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17
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0012849027
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For the preparation and reaction of menthone as a chiral auxiliary in dioxinone chemistry, see: a) M. Sato, K. Takayama, T. Furuya, N. Inukai, T. Kato, Chem. Pharm. Bull. 1987, 35, 3971-3974;
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18
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0001435632
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b) M. Demuth, A. Palomer, H. D. Sluma. A. K. Dey, C. Kruger, Y. H. Tsay, Angew. Chem. 1986, 98, 1093-1095;
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21
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37049133322
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a) J. A. Osborn, F. H. Jardine, J. F. Young, G. Wilkinson, J. Chem. Soc. 1966, 1711-1732;
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23
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33947721706
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24
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25
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31944450636
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b) S. Bell, B. Wüstenberg, S. Kaiser. F. Menges. T. Netscher. A. Pfaltz, Science 2006, 311, 642-644.
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27
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75749110451
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It is noted that regioisomer 18' underwent the hydrogenation with slightly lower stereoselectivity and in lower yield. A side product was obtained that was derived from tetrahydropyran formation as well as the deacetonization/decarboxylation as shown below. (Figure Presented)
-
It is noted that regioisomer 18' underwent the hydrogenation with slightly lower stereoselectivity and in lower yield. A side product was obtained that was derived from tetrahydropyran formation as well as the deacetonization/decarboxylation as shown below. (Figure Presented)
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-
-
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28
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67649499994
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For the hydrogenation of substrates that contain C-I bonding, a report has been published on the tolerance of vinyl iodide to hydrogenation over Crabtree's catalyst
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For the hydrogenation of substrates that contain C-I bonding, a report has been published on the tolerance of vinyl iodide to hydrogenation over Crabtree's catalyst: R. W. Denton, K. A. Parker, Org. Lett. 2009, 11, 2722-2723.
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Denton, R.W.1
Parker, K.A.2
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29
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75749120016
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The absolute and relative configuration of 19 was verified by Xray analysis at the stage of 24
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The absolute and relative configuration of 19 was verified by Xray analysis at the stage of 24.
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30
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0038475226
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Formation of the disubstituted epoxide is known to be kinetically preferable to formation of the primary epoxide
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Formation of the disubstituted epoxide is known to be kinetically preferable to formation of the primary epoxide: R. M. Hanson, Org. React. 2002, 60, 1-156.
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Hanson, R.M.1
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34
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75749087890
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CCDC 756980 (24) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
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CCDC 756980 (24) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www. ccdc.cam.ac.uk/data-request/cif.
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35
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0025847481
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36
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75749132296
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For the preparation of phenol 25; see the Supporting Information.
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For the preparation of phenol 25; see the Supporting Information.
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37
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75749137618
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Other protecting groups that were tested but did not allow the final deprotection include: benzyl2,4-dimethoxybenzyl, and 3,4-dimethoxybenzyl groups. This was presumably owing to the susceptibility of the epoxide and the tetramic acid moieties under hydrogenolytic, acidic (TFA), or oxidative (DDQ or cerium ammonium nitrate) conditions
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Other protecting groups that were tested but did not allow the final deprotection include: benzyl, 2,4-dimethoxybenzyl, and 3,4-dimethoxybenzyl groups. This was presumably owing to the susceptibility of the epoxide and the tetramic acid moieties under hydrogenolytic, acidic (TFA), or oxidative (DDQ or cerium ammonium nitrate) conditions.
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