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1
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(a) Sakabe, N.; Goto, T.; Hirata, Y. Tetrahedron 1977, 33, 3077-3081.
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Sakabe, N.1
Goto, T.2
Hirata, Y.3
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2
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0021128807
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(b) Shizuri, Y.; Nishiyama, S.; Imai, D.; Yamamura, S.; Furukawa, H.; Kawai, K.; Okada, N. Tetrahedron Lett. 1984, 25, 4771-4774.
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Shizuri, Y.1
Nishiyama, S.2
Imai, D.3
Yamamura, S.4
Furukawa, H.5
Kawai, K.6
Okada, N.7
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3
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0000639869
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(a) Boyer, P. D.; Chance, B.; Ernster, L.; Mitchell, P.; Racker, E.; Slater, E. C. Annu. Rev. Biochem. 1977, 46, 955-1026.
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Boyer, P.D.1
Chance, B.2
Ernster, L.3
Mitchell, P.4
Racker, E.5
Slater, E.C.6
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6
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0017673035
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(d) Muller, J. L. M.; Rosing, J.; Slater, E. C. Biochim. Biophys. Acta 1977, 462, 422-437.
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Muller, J.L.M.1
Rosing, J.2
Slater, E.C.3
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7
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0019511129
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(e) Gause, E. M.; Buck, M. A.; Douglas, M. G. J. Biol. Chem. 1981, 256, 557-562.
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Gause, E.M.1
Buck, M.A.2
Douglas, M.G.3
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8
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0021225970
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The synthesis of asteltoxin by Schreiber and Satake is an early notable example: Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1984, 106, 4186-4188.
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J. Am. Chem. Soc.
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Schreiber, S.L.1
Satake, K.2
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11
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0021997091
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(c) Bowden, M. C.; Patel, P.; Pattenden, G. Tetrahedron Lett. 1985, 26, 4793-4796.
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Bowden, M.C.1
Patel, P.2
Pattenden, G.3
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12
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37049078637
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(d) Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans, 1 1991, 1947-1950.
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Bowden, M.C.1
Patel, P.2
Pattenden, G.3
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13
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37049079711
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(e) Begley, M. J.; Bowden, M. C.; Patel, P.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1951-1958.
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Begley, M.J.1
Bowden, M.C.2
Patel, P.3
Pattenden, G.4
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15
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0021931895
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(-)-Citreoviridin and (+)-citreoviral: (a) Nishiyama, S.; Shizuri, Y.; Yamamura, S. Tetrahedron Lett. 1985, 26, 231-234.
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Nishiyama, S.1
Shizuri, Y.2
Yamamura, S.3
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17
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0013300559
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(c) Whang, K.; Venkataraman, H.; Kim, Y. G.; Cha, J. K. J. Org. Chem. 1991, 56, 7174-7177.
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Whang, K.1
Venkataraman, H.2
Kim, Y.G.3
Cha, J.K.4
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18
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0000031194
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(+)-Citreoviral: (d) Hatakeyama, S.; Matsui, Y.; Suzuki, M.; Sakurai, K.; Takano, S. Tetrahedron Lett. 1985, 26, 6485-6488.
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Tetrahedron Lett.
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Hatakeyama, S.1
Matsui, Y.2
Suzuki, M.3
Sakurai, K.4
Takano, S.5
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23
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0000687526
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See, inter alia: (a) Grese, T. A.; Hutchinson, K. D.; Overman, L. E. J. Org. Chem. 1993, 55, 2468-2477.
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J. Org. Chem.
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Grese, T.A.1
Hutchinson, K.D.2
Overman, L.E.3
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25
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0001122697
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Trost, B. M., Heathcock, C. H., Eds.; Pergamon: Oxford
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Colvin, E. W. In Comprehensive Organic Synthesis: Trost, B. M., Heathcock, C. H., Eds.; Pergamon: Oxford, 1992: Vol. 7, pp 641-651.
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(1992)
Comprehensive Organic Synthesis
, vol.7
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Colvin, E.W.1
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27
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85037520595
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note
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6c
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28
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85037521348
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note
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Stereochemical assignments for tetrahydrofuran products 13 and 14 were secured by nOe experiments. Details are provided in Supporting Information.
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29
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0001312398
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Available in 89% yield from silylation of 1-lithiopropyne: Meinke, P. T.; Krafft, G. A.; Guram, A. J. Org. Chem. 1988, 53, 3632-3634.
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(1988)
J. Org. Chem.
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Meinke, P.T.1
Krafft, G.A.2
Guram, A.3
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30
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0001155109
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Kataoka, Y.; Miyai, J.; Oshima, K.; Takai, K.; Utimoto, K. J. Org. Chem. 1992, 57, 1973-1981.
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J. Org. Chem.
, vol.57
, pp. 1973-1981
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Kataoka, Y.1
Miyai, J.2
Oshima, K.3
Takai, K.4
Utimoto, K.5
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31
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0000787875
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Nemoto, H.; Ishibashi, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1992, 57, 1707-1712.
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J. Org. Chem.
, vol.57
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Nemoto, H.1
Ishibashi, H.2
Nagamochi, M.3
Fukumoto, K.4
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32
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0000169587
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Tsunoda, T.; Suzuki, M.; Noyori, R. Tetrahedron Lett. 1980, 21, 1357-1358.
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(1980)
Tetrahedron Lett.
, vol.21
, pp. 1357-1358
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Tsunoda, T.1
Suzuki, M.2
Noyori, R.3
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33
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85037492126
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note
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16 from condensation of 19 with the more accessible secondary trimethylsilyl ether group of 20 undergoes Prins cyclization faster than it is trapped by the proximal tertiary trimethylsilyl ether.
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34
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0001712252
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Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354-5365.
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J. Am. Chem. Soc.
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Hopkins, M.H.1
Overman, L.E.2
Rishton, G.M.3
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35
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85037493312
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note
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A tetrahydrofuran product epimeric to 22 at C5 was not detected in this reaction or in the initial condensation of 19 and 20.
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36
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85037519811
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note
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The enantiopurity of 22 was confirmed by HPLC analysis using a Chiralcel OD column.
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37
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3643127470
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Fleming, I.; Henning, R.; Flaut, H. J. Chem. Soc., Chem. Commun. 1984, 29-31.
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J. Chem. Soc., Chem. Commun.
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Fleming, I.1
Henning, R.2
Flaut, H.3
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39
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0028814797
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Taber, D. F.; Yet, L.; Bhamidipati, R. S. Tetrahedron Lett. 1995, 36, 351-354.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 351-354
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Taber, D.F.1
Yet, L.2
Bhamidipati, R.S.3
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40
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85037508407
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note
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At this point, the constitution of the tetrahydrofuran produced upon Prins-pinacol rearrangement was rigorously established by single-crystal X-ray analysis of the phenylcarbamate derivative.
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41
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84889491424
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Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett 1990, 533-535.
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(1990)
Synlett
, pp. 533-535
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Cooper, M.S.1
Heaney, H.2
Newbold, A.J.3
Sanderson, W.R.4
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43
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85037514597
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note
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5c have been reported for 1.
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44
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85037492194
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note
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29
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45
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0030877492
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For other reports documenting the high rate of the pinacol rearrangement step in Prins-pinacol rearrangements, see: (a) Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927-8940.
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(1997)
Tetrahedron
, vol.53
, pp. 8927-8940
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Minor, K.P.1
Overman, L.E.2
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