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note
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11 and Snider (Snider, B. B. Personal communication to L.E.O., July 21, 1998) suggest that the stereochemistry of batzelladine F at C4 and C9 is epimeric to that shown in Figure 1.
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Snider, B. B.; Chen, J.; Patil, A. D.; Freyer, A. J. Tetrahedron Lett. 1996, 37, 6977.
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and references to earlier papers from the Murphy group cited therein
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Black, G.P.1
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0344501254
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Orlando, FL; American Chemical Society: Washington, DC, ORG 139
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0344501253
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note
-
It should be noted that an insoluble, though labile, intermediate of unknown structure is formed within 1 h when the Biginelli condensation of 24a and allyl acetoacetate was performed in THF. Although this intermediate provided 25b and 26b when reexposed to the reaction conditions in both THF and trifluoroethanol, the diastereoselectivity of the trifluoroethanol reaction dropped below that of the reaction performed in THF.
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-
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34
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0345363614
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note
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37
-
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-
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35
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0031584880
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For a recent mechanistic study of the classical Biginelli condensation of aldehydes, β-ketoesters, and urea in the presence of HCl, see: Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.
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37
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0345363612
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Personal communication to L.E.O., July 19
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Snider, B. B. Personal communication to L.E.O., July 19, 1996.
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Snider, B.B.1
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0345363613
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note
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40
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43
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0344070081
-
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note
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Since the counterion of 10 derived from natural batzelladine A is not described, the significance, if any, of this 30% discrepancy in rotation magnitude is unknown.
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-
-
-
44
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0344070079
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-
To be submitted for publication
-
An improved route to the 2a,8a-anti series employing an alternate tethered Biginelli construction of the 4,7-disubstituted-1,2,2a,5,6,7,8,8a-octahydro-5,6,8b-triazaacenaphthylenium-3- carboxylate unit has been developed: Ly, S. K.; Overman, L. E. To be submitted for publication.
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Ly, S.K.1
Overman, L.E.2
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46
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