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0038585939
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note
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(a) Early studies involved the use of uridine as a starting material, with the intention of utilizing an asymmetric Ugi condensation or an asymmetric Strecker reaction as the key operation. Unfortunately, the required imine derivatives were either unstable or resulted in poor selectivity upon nucleophilic addition. In the ribose series, the key stereocenter could be formed using a chiral auxiliary-mediated Strecker reaction, but the resulting amino-nitrile could not be hydrolyzed.
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33
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38849119887
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0000409113
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(d) For an auxiliary-based Strecker reaction, see: Davis, F. A.; Portonovo, P. S.; Reddy, R. E.; Chiu, Y.-H. J. Org. Chem. 1996, 61, 440.
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0038585932
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For a study of the addition of allylmetal reagents to aldehyde 3, see: Danishefsky, S. J.; Deninno, M. P.; Phillips, G. B.; Zelle, R. E.; Lartey, P. A. Tetrahedron 1986, 42, 2.
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41
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0038585933
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note
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Attempted use of the zinc acetylide addition with a uridine-derived aldehyde was thwarted by a complete lack of reactivity with a variety of alkynes.
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42
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84981848681
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Alcohol 2 was prepared on a 30-gram scale in 79% yield by a modification of the procedure found in: Leonard, N. J.; Carraway, K. L. J. Heterocycl. Chem. 1966, 3, 485.
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44
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0037571667
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note
-
3/pyridine, TPAP, IBX/DMSO, Dess-Martin) proved to be much less reliable for this transformation, being difficult to reproduce and providing aldehyde of lower purity than with IBX.
-
-
-
-
45
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0038247315
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note
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5N 322.1654, found 322.1657.
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