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2
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0343052006
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note
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We appreciate a referee's suggestion that the second reaction of our tandem process, particularly in a case such as 2a where a five-membered ring is formed, is more properly called a Prins reaction rather than an ene reaction.
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3
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0343923697
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For a tandem Prins-pinacol rearrangement process, see: (a) Ando, S.; Minor, K. P.; Overman, L. E. J. Org. Chem. 1997, 62, 6376.
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Ando, S.1
Minor, K.P.2
Overman, L.E.3
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6
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33947093975
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Pinacol rearrangement of a Diels-Alder derived bicyclo[2.2.2]-octene has previously been exploited in the syntheses of various natural products: (a) Monti, S. A.; Chen, S.; Yang, Y.; Yuan, S.; Bourgeois, O. P. J. Org. Chem. 1978, 43, 4062.
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Monti, S.A.1
Chen, S.2
Yang, Y.3
Yuan, S.4
Bourgeois, O.P.5
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8
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0015101797
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Daly, J. W.; Karle, I.; Myers, C. W.; Tokuyama, T.; Waters, J. A.; Wikop, B. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1870.
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Daly, J.W.1
Karle, I.2
Myers, C.W.3
Tokuyama, T.4
Waters, J.A.5
Wikop, B.6
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10
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0016064713
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(b) Albuquerque, E. X.; Kuba, K.; Daly, J. W. J. Pharmacol. Exp. Therap. 1974, 189, 513.
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Albuquerque, E.X.1
Kuba, K.2
Daly, J.W.3
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11
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0033606247
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(a) For a recent synthesis of (-)-histrionicotoxin by using a tandem process as a key step, see Williams, G. M.; Roughley, S. D.; Davies, J. E.; Holmes, A. B. J. Am. Chem. Soc. 1999, 121, 4900.
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Williams, G.M.1
Roughley, S.D.2
Davies, J.E.3
Holmes, A.B.4
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12
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0033597912
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and references cited
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(b) For a recent synthesis of perhydrohistrionicotoxin, see; Luzzio, F. A.; Fitch, R. W. J. Org. Chem. 1999, 64, 5485 and references cited.
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Luzzio, F.A.1
Fitch, R.W.2
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13
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0032474797
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For a good review with citations to recent work, see: Tanner, D.; Hagberg, L. Tetrahedron 1998, 54, 7907.
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Tetrahedron
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Tanner, D.1
Hagberg, L.2
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0342617765
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For a comprehensive review on studies before 1989, see: Kotera, M. Bull. Soc. Chim. Fr. 1989, 370.
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Kotera, M.1
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15
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0007322358
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Part of this work has been published in preliminary form, see: Kim, D.; Hong, S. W.; Park, C. W. J. Chem. Soc., Chem. Commun. 1997, 21, 2263.
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Kim, D.1
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Park, C.W.3
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16
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0019808505
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(a) Ibuka, T.; Mitsui, Y.; Hayashi, K.; Minakata, H.; Inubushi, Y. Tetrahedron Lett. 1981, 22, 4425.
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Ibuka, T.1
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17
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0016654332
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(b) Corey, E. J.; Arnett, J. F.; Widiger, G. N. J. Am. Chem. Soc. 1975, 97, 430.
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Corey, E.J.1
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Widiger, G.N.3
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0343923666
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note
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5
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21
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0343051970
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note
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Similarly, the application of a tandem pinacol rearrangement-ene reaction to the endo alcohol 31a led to the desired six-membered tricyclic ketone 32a as the major isomer (88:12). (Matrix presentation)
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24
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0001498171
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Matlin, A. R.; George, C. F.; Wolff, S.; Agosta, W. C. J. Am. Chem. Soc. 1986, 108, 3385.
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Matlin, A.R.1
George, C.F.2
Wolff, S.3
Agosta, W.C.4
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25
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0343051965
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For an example of the reduction of an alkene during a modified Wolff-Kishner reduction, see: McIntosh, J. M. Can. J. Chem. 1979, 57, 2114.
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McIntosh, J.M.1
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4544245333
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Trost, B. M., Ed; Pergamon Press: New York
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(a) Krow, G. R. Comprehensive Organic Synthesis; Trost, B. M., Ed; Pergamon Press: New York, 1991; Vol. 7, p 673.
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Krow, G.R.1
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Davis, F. A.; Vishwaskarma, L. C.; Bilimers, J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241.
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Davis, F.A.1
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Finn, J.4
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