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Maring, C.; McDaniel, K.; Krueger, A.; Ahau, C.; Sun, M.; Madigan, D.; DeGoey, D.; Chen, H.-J.; Yeung, M. C.; Flosi, W.; Grampovnik, D.; Kati, W.; Klein, L.; Stewart, K.; Stoll, V.; Saldivar, S.; Montgomery, D.; Carrick, R.; Steffy, K. Kempf, D.; Molla, A.; Kohlbrenner, W.; Kennedy, A.; Herrin, T.; Xu, Y.; Laver, W.G. In Presented at 14th International Conference on Antiviral Research, Antiviral Research 2001, 50, A76; Abstract 129.
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38349147318
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Raja, S. N.; George, K. S. T.; Fan, L.; Nequist, G.; Reisch, T.; Maring, C.; McDaniel, K.; DeGoy, D.; Darbyshire, K. Abstracts of Papers, 41st Interscience Conference on Antimicrobial Agents and chemotherapy, Chicago, IL; American Society for Microbiology: Washington, DC, 2001; Abstract F-1683.
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DeGoey D.A., Chen H.-J., Flosi W.J., Grampovnik D.J., Yeung C.M., Klein L.L., and Kempf D.J. J. Org. Chem. 67 (2002) 5445-5453
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Klein, L.L.6
Kempf, D.J.7
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0242541885
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Barnes D.M., Bhagavatula L., Demattei J., Gupta A., Hill D.R., Manna S., McLaughlin M.A., Nichols P., Premchandran R., Rasmussen M.W., Tian Z., and Wittenberger S.J. Tetrahedron: Asymmetry 14 (2003) 3541-3551
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McLaughlin, M.A.7
Nichols, P.8
Premchandran, R.9
Rasmussen, M.W.10
Tian, Z.11
Wittenberger, S.J.12
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9
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33646064214
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For an excellent review on Overman rearrangement and related reactions, see:. Overman L.E. (Ed), Wiley, New York, NY
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For an excellent review on Overman rearrangement and related reactions, see:. Overman L.E., and Carpenter N.E. In: Overman L.E. (Ed). Organic Reactions Vol. 66 (2005), Wiley, New York, NY 1-107
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Overman, L.E.1
Carpenter, N.E.2
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10
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0001923963
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Recent representative reports on the Overman rearrangement and the related sigmatropic rearrangement of allylic secondary alcohols, see:
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Recent representative reports on the Overman rearrangement and the related sigmatropic rearrangement of allylic secondary alcohols, see:. Savage I., Thomas E.J., and Wilson P.D. J. Chem. Soc., Perkin Trans. 1 (1999) 3291-3303
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J. Chem. Soc., Perkin Trans. 1
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Savage, I.1
Thomas, E.J.2
Wilson, P.D.3
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12
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0037189268
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Roulland E., Monneret C., Florent J.-C., Bennejean C., Renard P., and Léonce S. J. Org. Chem. 67 (2002) 4399-4406
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J. Org. Chem.
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Roulland, E.1
Monneret, C.2
Florent, J.-C.3
Bennejean, C.4
Renard, P.5
Léonce, S.6
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16
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0035036118
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Report of the successful cascade Overman rearrangement on 1,2-dihydroxy-3-cyclohexene, see:
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Report of the successful cascade Overman rearrangement on 1,2-dihydroxy-3-cyclohexene, see:. Demay S., Kotschy A., and Knochel P. Synthesis (2001) 863-866
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Synthesis
, pp. 863-866
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Demay, S.1
Kotschy, A.2
Knochel, P.3
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17
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33846311745
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Construction of diamines from allylic 1,2-diols by the stepwise sigmatropic rearrangement, see:
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Construction of diamines from allylic 1,2-diols by the stepwise sigmatropic rearrangement, see:. Ichikawa Y., Egawa H., Ito T., Isobe M., Nakano K., and Kotsuki H. Org. Lett. 8 (2006) 5737-5740
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Org. Lett.
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Ichikawa, Y.1
Egawa, H.2
Ito, T.3
Isobe, M.4
Nakano, K.5
Kotsuki, H.6
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28844503703
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Dimopoulos P., Athlan A., Manaviazar S., George J., Walters M., Lazarides L., Aliev A.E., and Hale K.J. Org. Lett. 7 (2005) 5369-5372
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Dimopoulos, P.1
Athlan, A.2
Manaviazar, S.3
George, J.4
Walters, M.5
Lazarides, L.6
Aliev, A.E.7
Hale, K.J.8
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20
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0029041556
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Komiotis D., Pananookooln S., Zaw K., Dieter J.P., Le Breton G.C., and Venton D.L. Eur. J. Med. Chem. 30 (1995) 321-326
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Komiotis, D.1
Pananookooln, S.2
Zaw, K.3
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0034903277
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Ando K. Synlett (2001) 1272-1274
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Synlett
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Ando, K.1
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23
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38349129071
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note
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13C NMR, IR and mass spectrometric and/or elemental analyses.
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24
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38349163280
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note
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A similar reaction of the E-isomer of 9 with methylmagnesium bromide, in which the chelation of magnesium between the carbonyl and the dioxolane ring is geometrically impossible, produced a mixture (ca. 1.5:1) of tertiary alcohols.
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26
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0034119149
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see also
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see also,. Cho C.-G., Lim Y.-K., Lee K.-S., Jung I.-H., and Yoon M.-Y. Synth. Commun. 30 (2000) 1643-1650
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Synth. Commun.
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Cho, C.-G.1
Lim, Y.-K.2
Lee, K.-S.3
Jung, I.-H.4
Yoon, M.-Y.5
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27
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0032849512
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Zheng B.-Z., Maeda H., Mori M., Kusaka S., Yonemitsu O., Matsushima T., Nakajima N., and Uenishi J. Chem. Pharm. Bull. 47 (1999) 1288-1296
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Zheng, B.-Z.1
Maeda, H.2
Mori, M.3
Kusaka, S.4
Yonemitsu, O.5
Matsushima, T.6
Nakajima, N.7
Uenishi, J.8
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29
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38349115045
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note
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It was found that in the Wittig reaction of 17, the reaction temperature is important for the high Z-selectivity. When the reaction was carried out at 0 °C, a mixture of the Z- and E-isomers (ca. 10:1) was obtained.
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38349137948
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Some representative reports on the cascade sigmatropic rearrangement, see:
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Some representative reports on the cascade sigmatropic rearrangement, see:. Thamos A.F. J. Am. Chem. Soc. 91 (1969) 3281-3283
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(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 3281-3283
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Thamos, A.F.1
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0043160317
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Tisdale E.J., Vong B.G., Li H., Kim S.H., Chowdhury C., and Theodorakis E.A. Tetrahedron 59 (2003) 6873-6887
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Tisdale, E.J.1
Vong, B.G.2
Li, H.3
Kim, S.H.4
Chowdhury, C.5
Theodorakis, E.A.6
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36
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35048814051
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Nicolaou K.C., Lister T., Denton R.M., and Gelin C.F. Angew. Chem., Int. Ed. 46 (2007) 7501-7505
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Nicolaou, K.C.1
Lister, T.2
Denton, R.M.3
Gelin, C.F.4
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37249082658
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Recently, we have reported the synthesis of (-)-morphine utilizing the cascade Claisen rearrangement of a cyclohexene-diol derivative. See, Tanimoto, H.; Saito, R.; Chida, N. Tetrahedron Lett. 2008, 49, 358-362.
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