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44
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0345421520
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note
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3 solution.
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45
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0000167908
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46
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0141855021
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This is in accordance with the recent report by West who describes the need for more forcing conditions to effect the tandem Nazarov cyclization [4 + 3]-trapping of a cyclopenta-fused dienone: (a) Wang, Y.; Schill, B. D.; Arif, A. M.; West, F. G. Org. Lett. 2003, 5, 2747-2750.
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Wang, Y.1
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47
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0034958711
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Also, the same author has found that solvent trapping of photochemically generated pyran-4-ones does not occur in the case of cyclopenta-fused systems, again because of unacceptable levels of ring strain in the hypothetical oxyallyl zwitterion: (b) Fleming, M.; Fisher, P. V.; Gunawardena, G. U.; Jin, Y.; Zhang, C.; Zhang, W.; Arif, A. M.; West, F. G. Synthesis 2001, 1268-1274.
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48
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0344990454
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note
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We tested γ-butyrolactone, α-angelicalactone, γ-valerolactone, and α-acetil-γ-butyrolactone under different experimental conditions (addition of the base to the lactone or lactone to the base, several molar ratios up to 4 equiv of base, reaction temperatures from -78 °C to room temperature, reaction times from 30 min to 20 h).
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49
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0344990452
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note
-
In the case of product 35, hydrolysis conditions must be carefully controlled in order to avoid the side hydrolysis of the cyclic vinyl ether moiety with subsequent opening of the seven-membered cycle. In this case (7E)-7-ethoxy-7,9-decadien-1-ol was recovered.
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54
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0345421519
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note
-
The oxidation was carried out on the crude mixtures obtained after workup of the N protection reactions. Although the overall yields were not satisfactory, we did not try at this stage to optimize them or evaluate other procedures to obtain these lactams.
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55
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0003480898
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Pergamon Press: Oxford, U.K.
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1H NMR spectrum. In particular, the two methyl groups resonate very close at 1.14 and 1.11 ppm which hampers the determination of their relative orientation by NOE studies. On the other hand, the signals of H4 (2.61 ppm) and H5 (2.86 ppm) are distinct but that of H4 in part overlaps with the signal (at 2.65 ppm) of a proton on C6. To distinguish between scalar and spatial interactions, a series of NOESY spectra were recorded by progressively changing the mixing time. In this way a NOESY cross-peak between H4 and H5 could be identified. Derome, A. E. Modern NMR Techniques for Chemistry Reserach; Pergamon Press: Oxford, U.K., 1987.
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