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38
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0034638388
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3)).
-
3)).
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39
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0028926606
-
-
3)).
-
3)).
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40
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37049057911
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For examples of the diastereoselective addition of organometallic reagents to αl-chloro aldehydes see: (a) Cornforth, J. W, Cornforth, R. H, Mathew, K. K. J. Chem. Soc. 1959, 112
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41
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33644959351
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For a theoretical investigation of nucleophilic addition to an α-chloro aldehyde see:, and references therein
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47
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0034612880
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For the diastereoselective addition of optically pure lithio-vinyl sulfoxides to a racemic α-chloro aldehyde see: Marino, J. P, Anna, L. J, Fernández de la Pradilla, R, Martinez, M. V, Montero, C, Viso, A. J. Org. Chem. 2000, 65, 6462
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For the diastereoselective addition of optically pure lithio-vinyl sulfoxides to a racemic α-chloro aldehyde see: Marino, J. P.; Anna, L. J.; Fernández de la Pradilla, R.; Martinez, M. V.; Montero, C.; Viso, A. J. Org. Chem. 2000, 65, 6462.
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-
-
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48
-
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36849093293
-
-
2, EtOH) in excellent yield (94%).
-
2, EtOH) in excellent yield (94%).
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-
-
-
49
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36849014680
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-
D values with those in the literature (see Supporting Information), indicating that there is no erosion of optical purity during the 1,2-addition reactions (10 → 18a-f).
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D values with those in the literature (see Supporting Information), indicating that there is no erosion of optical purity during the 1,2-addition reactions (10 → 18a-f).
-
-
-
-
50
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0033525048
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Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866.
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Matsumori, N.1
Kaneno, D.2
Murata, M.3
Nakamura, H.4
Tachibana, K.5
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51
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0032564684
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1H NMR spectrum of 19f precluded nOe analysis; however, their chemical shift is consistent with those reported for the H4/H5 resonances in trans-(4S,5S)4,5-epoxynonane (δ 2.61-2.70 ppm) and differ significantly from those reported for cis-(4S,5R)-4,5-epoxynonane δ 2.87-2.96 ppm) in: Besse, P.; Sokoltchik, T.; Veschambre, H. Tetrahedron: Asymmetry 1998, 9, 4441.
-
1H NMR spectrum of 19f precluded nOe analysis; however, their chemical shift is consistent with those reported for the H4/H5 resonances in trans-(4S,5S)4,5-epoxynonane (δ 2.61-2.70 ppm) and differ significantly from those reported for cis-(4S,5R)-4,5-epoxynonane δ 2.87-2.96 ppm) in: Besse, P.; Sokoltchik, T.; Veschambre, H. Tetrahedron: Asymmetry 1998, 9, 4441.
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52
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0030971917
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Gries, G.; Slessor, K. N.; Gries, G.; Khaskin, G.; Wimalaratne, P. D. C.; Gray, T. G.; Grant, G. G.; Tracey, A. S.; Hulme, M. J. Chem. Ecol. 1997, 23, 19.
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Gries, G.1
Slessor, K.N.2
Gries, G.3
Khaskin, G.4
Wimalaratne, P.D.C.5
Gray, T.G.6
Grant, G.G.7
Tracey, A.S.8
Hulme, M.9
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53
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36849079208
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-
6.7 alkene function in 26. Lindlar reduction of 25 or 26 at room temperature led to the production of unidentified byproducts.
-
6.7 alkene function in 26. Lindlar reduction of 25 or 26 at room temperature led to the production of unidentified byproducts.
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54
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36849027071
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We thank Professor Gerhard Gries for kindly providing an authentic sample of, -1 and Regine Gries for carrying out the comparative GC analysis with our synthetic material
-
We thank Professor Gerhard Gries for kindly providing an authentic sample of ( - )-1 and Regine Gries for carrying out the comparative GC analysis with our synthetic material.
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55
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36849066838
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Field-studies will be carried out by the Forest Research Institute in Eberswalde, Germany. The results of these studies will be published in due course
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Field-studies will be carried out by the Forest Research Institute in Eberswalde, Germany. The results of these studies will be published in due course.
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