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0038728739
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note
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At the present writing, it is not clear to us why the reduction of 2 is significantly more selective than the model cases in ref 9, which bear substitution at the β-carbon of the olefin.
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22
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0001413313
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(a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
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26
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0004003407
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Elsevier, Amsterdam
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(a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
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Brandsma, L.1
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0034604562
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(a) Chodkiewicz, W. Ann. Chim. Paris 1957, 2, 819. (b) Chodkiewicz, W. Chemistry of Acetylenes; Viehe, H. G., Ed.; Marcel Deker: New York, 1969; p 597. (c) Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; pp 212-214. For recent work in this area, see: (d) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632.
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Angew. Chem., Int. Ed
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Siemsen, P.1
Livingston, R.C.2
Diederich, F.3
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0038390570
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note
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We thank Dr. Yun-Lian Lin, National Research institute of Chinese Medicine, Taipei 112, Taiwan, for sending us a specimen sample of panaxytriol.
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3).
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0037714457
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note
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20 For the absolute configuration of panaxytriol to be opposite to that shown, all of these precedents would have to be inapplicable.
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0038052256
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note
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A related Cadiot-Chodkiewicz cross-coupling reaction was reported in the process of total synthesis of panaxytriol (ref 7b). The novelty of our case lies in its application to a setting containing three nonprotected resident hydroxyl groups.
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