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25
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33646095701
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Preliminary data on this work were presented at the 2nd International Conference on Multi Component Reactions, Combinatorial and Related Chemistry (MCR2003), Genova (I), April 14-16, 2003.
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27
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33646108782
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note
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The triple bond is versatile since it can be exploited as precursor of both Z and E alkenes.
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28
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0032497590
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Hubschwerlen C., Angehrn P., Gubernator K., Page M.G.P., and Specklin J.-L. J. Med. Chem. 41 (1998) 3972-3975
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Hubschwerlen, C.1
Angehrn, P.2
Gubernator, K.3
Page, M.G.P.4
Specklin, J.-L.5
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29
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33646080304
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note
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For minimizing the elimination we usually preferred to stop the reaction before all 13 was consumed, since it was easily recovered and recycled.
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30
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33646101427
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note
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Treatment with TsCl in pyridine did not promote any reaction and for this reason we added 4-dimethylaminopyridine.
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32
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33646085965
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note
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Since 24 and 25 are racemic, the absolute configuration of them was arbitrarily reported in Scheme 5.
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33
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33646098107
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note
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It is noteworthy that, in order to get the highest reproducibility in the synthesis of 24a,b on preparative scale from 21, the reaction has to be performed employing a solution of LiHMDS in THF, freshly prepared by dissolving solid commercial LiHMDS.
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34
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37049067860
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Kinsman R., Lathbury D., Vernon P., and Gallagher T. J. Chem. Soc., Chem. Commun. (1987) 243-244
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(1987)
J. Chem. Soc., Chem. Commun.
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Kinsman, R.1
Lathbury, D.2
Vernon, P.3
Gallagher, T.4
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37
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33646086189
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note
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The whole sequence was first tested on the 70:30 diastereomeric mixture of 24a,b, to give 29a,b without appreciable changes in dr and then on the separated diastereoisomers.
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38
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33646105559
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note
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Intermediate monoalcohol was difficult to be recovered by extractive work up, due to its high affinity for water, and since it was nearly impossible to evidentiate its spot on TLC.
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