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85038540771
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note
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14. All new compounds except volatile compounds were spectroscopically characterized and furnished satisfactory elemental analyses (C, H, N, ± 0.3%) or high-resolution mass spectra. See in the experimental section.
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22
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15. Evans, D. A.; Britton, T. C.; Ellma, J. A. Tetrahedron Lett. 1987, 28, 6141.
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0001616071
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25
-
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85038552204
-
-
note
-
34 was also examined, but the yield was poor because of the by-product formations.
-
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26
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0000192963
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19. a) Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
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0015137107
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8 methyl group. See: a) Kinoshita, M.; Wada, M.; Aburagi, S.; Umezawa, S. J. Antibiot. 1971, 24, 724.
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0001624218
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b) Kinoshita, M.; Aburagi, S.; Wada, M.; Umezawa, S. Bull. Chem. Soc. Jpn. 1973, 46, 1279.
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0027172456
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23. Trécourt, F.; Mallet, M.; Mongin, O.; Gervais, B.; Quéguiner, G. Tetrahedron 1993, 49, 8373.
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Quéguiner, G.5
-
36
-
-
85038551927
-
-
note
-
25. 4-lodo-3-methoxymethoxypyridine was also prepared with 1,2-diiodo-1,1,2,2-tetrafluoroethane, but the next methoxy replacement was not as good as the case of 4-bromo-3-methoxymethoxypyridine because of the reductive deiodination by-reaction resulting in 3-methoxymethoxypyridine. It should also be noted that 4-bromo-3-methoxymethoxypyridine was much faster to react to NaOMe than 4-iodo-3-methoxymethoxypyridine, although the reason still remains unclear.
-
-
-
-
37
-
-
85038551785
-
-
note
-
26. Structure of UK-2A is depicted with the absolute stereochemistry found in our synthetic UK-2A.
-
-
-
-
38
-
-
85038554250
-
-
note
-
1H NMR of the synthesized γ-lactone 24 was different from the reported one. The coupling pattern of each signal in our γ-lactone 24 was very similar to the reported γ-lactone 24, however, the chemical shifts of some signals were not in accordance with those of the corresponding signals of the reported γ-lactone 24. Since γ-lactone 25 synthesized in our hands was identical with the reported γ-lactone 25, our γ-lactone 24 should be identical with the reported γ-lactone 24.
-
-
-
-
39
-
-
85038549799
-
-
note
-
28. Every candidate was calculated as the protonated form at the nitrogen in the pyridine ring.
-
-
-
-
40
-
-
84986512474
-
-
29. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187.
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Swaminathan, S.5
Karplus, M.6
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41
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0026847070
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30. a) Perez, J. J.; Villar, H. O.; Loew, G. H. J. Comp. Aided Molec. Design. 1992, 6, 175.
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Perez, J.J.1
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Loew, G.H.3
-
43
-
-
85038550057
-
-
note
-
31. Though we have postulated it would be reasonable that the enolization process started from the most stable conformer of each substrate, there might be a possibility that the transformation occurred from the less stable conformer of the starting substrate to the less stable one of the terminal product.
-
-
-
-
44
-
-
85038539166
-
-
note
-
10 because of the small amount of natural UK-3A. In the private communication from Prof. M. Taniguchi and Dr. O. Sakanaka, they were reported as δ 3.08 ppm and δ 65.1 ppm, respectively.
-
-
-
-
45
-
-
85038550709
-
-
note
-
4 segment in the nine-membered dilactone were both chiral, we believe that the optical purity of our γ-lactone 25 is excellent.
-
-
-
-
46
-
-
33845554892
-
-
34. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
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Evans, D.A.1
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Mathre, D.J.3
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