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Moore, R, E.; Cheuk, C.; Yang, X.-Q. G.; Patterson, G. M. L.; Bonjouklian, R.; Smitka, T. A.; Mynderse, J. S.; Foster, R. S.; Jones, N. D.; Swartzendruber, J. K.; Deeter, J. B. J. Org. Chem. 1987, 52, 1036-1043.
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Swartzendruber, J.K.10
Deeter, J.B.11
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0342263989
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0344334587
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0026606140
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8
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0027973653
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Smitka, T.A.8
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9
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0029569071
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0345629147
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note
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All of the extracts show antifungal activity against Asperigillus oryzae, Penicillium notatum, Saccharomyces cerevisiae, and Trichophyton mentagrophytes. The isonitriles are generally responsible for this activity.
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11
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0344766640
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note
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8 Because the CD spectra of 1 and 2 are similar in shape, 1 must have the same absolute stereochemisty as 2.
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-
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12
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0344334586
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note
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Dihedral angles were determined from molecular models generated from CS Chem3D Pro.
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13
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0024805170
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Naturally occurring chloroepoxides are known. (a) Nakanishi, S.; Ando, K; Kawamoto, I.; Yasuzawa,T.; Sano, H.; Kase, H. J. Antibiot. 1989, 42, 1775-1783.
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Nakanishi, S.1
Ando, K.2
Kawamoto, I.3
Yasuzawa, T.4
Sano, H.5
Kase, H.6
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15
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0027218296
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(c) Stadler, M.; Anke, H.; Bergquist, K.-E.; Sterner, O. J. Antibiot, 1993, 46, 968-971.
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Stadler, M.1
Anke, H.2
Bergquist, K.-E.3
Sterner, O.4
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16
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0020644063
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Reaction of 1-chlorocyclohexene oxide or its thermal rearrangement product 2-chlorocyclohexanone with a nucleophile results in the same product. For example, hydrolysis of either compound at 0-37°C leads quantitatively to 2-hydroxycyclohexanone. No significant rearrangement of the chloroepoxide to the aα-chloroketone occurs during the hydrolysis, as the rearrangement requires a higher temperature (80-100°C). Both compounds react with amines to give the same 2-aminocyclohexanones. Gold, B.; Leuschen, T. Chem.-Biol. Interact. 1983, 45, 305-314.
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Chem.-biol. Interact.
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Gold, B.1
Leuschen, T.2
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17
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33748898384
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A mixture of 1-chloro-cis- and -trans-4-methylcyclohexene oxide rearranges exclusively to trans-2-chloro-4-methylcyclohexanone at 80-100°C. A common α-keto carbonium ion-chloride ion-pair intermediate is proposed. McDonald, R. N.; Tabor, T. E. J. Am. Chem. Soc. 1967, 89, 6573-6578.
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McDonald, R.N.1
Tabor, T.E.2
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