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4NBr in acetone at rt for 24 h. New, J. S.; Christopher, W. L.; Yevich, J. P.; Butler, R.; Schlemmer, Jr., R. F.; VanderMaelen, C. P.; Cipollina, J. A. J. Med. Chem. 1989, 32, 1147-1156.
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84986705631
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Chromatographic separation of 5d and 6d was not possible and the mixture was still obtained after dehydration with p-TsOH and 4 Å molecular sieves in dichloromethane. For isolation of 5d, known as pyrrolam C, from culture broth of Streptomyces olivaceus and structural determination, see: Grote, R.; Zeeck, A.; Stümpfel, J.; Zähner, H. Liebig's Ann. Chem. 1990, 525-530.
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note
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1H-COSY experiments. Also, the relative stabilities of 6e, 6g and their regioisomers were estimated using MOPAC PM3 semiempirical calculations. These results suggest that thermodynamics control dehydration regiochemistry. (matrix presented)
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22
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85030194372
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Treatment of 4e or 4g with activated magnesium turnings in THF heated at reflux failed to give any cyclized product
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Treatment of 4e or 4g with activated magnesium turnings in THF heated at reflux failed to give any cyclized product.
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23
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85030186678
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note
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+, 90), 136(33), 122(58), 108(47), 95(100), 80(22), 67(25), 55(75).
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24
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Kayser, M. M.; Wipff, G. Can. J. Chem. 1982, 60, 1192-1198. Kayser, M. M.; Salvador, J.; Morand, P.; Krishnamurty, H. G. Can. J. Chem. 1982, 60, 1199-1206. Kayser, M. M.; Salvador, J. Morand, P.; Can. J. Chem. 1983, 61, 439-441.
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0000317301
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Kayser, M. M.; Wipff, G. Can. J. Chem. 1982, 60, 1192-1198. Kayser, M. M.; Salvador, J.; Morand, P.; Krishnamurty, H. G. Can. J. Chem. 1982, 60, 1199-1206. Kayser, M. M.; Salvador, J. Morand, P.; Can. J. Chem. 1983, 61, 439-441.
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