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1
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33646403425
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For a recent review of strategies for the formation of tetrahydropyran rings in the synthesis of natural products, see: (a) Clarke, P.A, Santos, S, Chem. 2006, 9, 2045
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For a recent review of strategies for the formation of tetrahydropyran rings in the synthesis of natural products, see: (a) Clarke, P.A.; Santos, S. Eur. J. Org. Chem. 2006, 9, 2045.
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2
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19044386185
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For examples of 2,6-disubstituted tetrahydropyrans in natural product synthesis, see: (b) Clarke, P. A, Martin, W. H. C. Tetrahedron 2005, 61, 5433
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For examples of 2,6-disubstituted tetrahydropyrans in natural product synthesis, see: (b) Clarke, P. A.; Martin, W. H. C. Tetrahedron 2005, 61, 5433.
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4
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0035852116
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(d) Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2001, 123, 12426.
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Corbett, R.M.3
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5
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8644289966
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For recent efforts toward the construction of tetrahydropyran rings, see: a
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For recent efforts toward the construction of tetrahydropyran rings, see: (a) Clarke, P. A.; Martin, W. H. C. Tetrahedron Lett. 2004, 45, 9061.
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Clarke, P.A.1
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So, B.3
Hong, J.4
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12
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0001309251
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For indium-mediated tetrahydropyran and dihydropyran syntheses, see: a
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For indium-mediated tetrahydropyran and dihydropyran syntheses, see: (a) Viswanathan, G. S.; Yang, J.; Li, C.-J. Org. Lett. 1999, 1, 993.
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0033605402
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(b) Yang, J.; Viswanathan, G. S.; Li, C.-J. Tetrahedron Lett. 1999, 40, 1627.
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Yang, J.1
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Li, C.-J.3
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16
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0037201123
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(e) Loh, T.-P.; Yang, J.-Y.; Feng, L.-C.; Zhou, Y. Tetrahedron Lett. 2002, 43, 7193.
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Tetrahedron Lett
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Loh, T.-P.1
Yang, J.-Y.2
Feng, L.-C.3
Zhou, Y.4
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19
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41149110099
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3N, THF; NaI, acetone) from the corresponding allylic alcohol: Trost, B. M.; Chan, D. M. T.; Nanninga, N. Org. Synth. 1984, 62, 58.
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3N, THF; NaI, acetone) from the corresponding allylic alcohol: Trost, B. M.; Chan, D. M. T.; Nanninga, N. Org. Synth. 1984, 62, 58.
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20
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34547844085
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Allatabakhsh, A.; Pham, M.; Minehan, T. G. Heterocycles 2007, 72, 115.
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Allatabakhsh, A.1
Pham, M.2
Minehan, T.G.3
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21
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41149112938
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For the spectral data of 2a, see ref 3e
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For the spectral data of 2a, see ref 3e.
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22
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41149096527
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Assessed by a simple litmus paper test
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Assessed by a simple litmus paper test.
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23
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41149159679
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As much as 50% of desilylated homoallylic alcohol was isolated from the reaction mixtures in some cases
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As much as 50% of desilylated homoallylic alcohol was isolated from the reaction mixtures in some cases.
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24
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31944435336
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For a discussion on erosion of enantioselectivity and side-chain exchange via the oxonium-Cope rearrangement in Prins reactions, see: (a) Cheng-Hsia, A. L, Loh, T.-P. Tetrahedron Lett. 2006, 47, 1641
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For a discussion on erosion of enantioselectivity and side-chain exchange via the oxonium-Cope rearrangement in Prins reactions, see: (a) Cheng-Hsia, A. L.; Loh, T.-P. Tetrahedron Lett. 2006, 47, 1641.
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25
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0001134456
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(b) Crosby, S. R.; Harding, J. R.; King, C. D.; Parker, G. D.; Willis, C. L. Org. Lett. 2002, 4, 577.
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Crosby, S.R.1
Harding, J.R.2
King, C.D.3
Parker, G.D.4
Willis, C.L.5
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26
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0013254056
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(c) Marumoto, S.; Jaber, J. J.; Vitale, J. P.; Rychnovsky, S. D. Org. Lett. 2002, 4, 3919.
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Marumoto, S.1
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Vitale, J.P.3
Rychnovsky, S.D.4
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27
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41149087251
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Chan et al. have presented evidence that the intermediate in aqueous indium-mediated allylation reactions is allylindium(I): Chan, T. H.; Yang, T. J. Am. Chem. Soc. 1999, 121, 3228.
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Chan et al. have presented evidence that the intermediate in aqueous indium-mediated allylation reactions is allylindium(I): Chan, T. H.; Yang, T. J. Am. Chem. Soc. 1999, 121, 3228.
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28
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41149176496
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2, 0°C) followed by iodide displacement (NaI, acetone, rt, 24 h).
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2, 0°C) followed by iodide displacement (NaI, acetone, rt, 24 h).
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29
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33750434264
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13C NMR) for 9 matched those reported by Hinkle for the same compound with syn-2,6- stereochemistry: (a) Lian, Y.; Hinkle, R. J. J. Org. Chem. 2006, 71, 7071.
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13C NMR) for 9 matched those reported by Hinkle for the same compound with syn-2,6- stereochemistry: (a) Lian, Y.; Hinkle, R. J. J. Org. Chem. 2006, 71, 7071.
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30
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33744791835
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Although Li reports the use of E-vinylsilanes for the synthesis of dihydropyrans (ref 3a, Brimble reports that the Z-configuration of the vinylsilane is crucial for the formation of dihydropyrans: (b) Meilert, K, Brimble, M. A. Org. Biolom. Chem. 2006, 4, 2184
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Although Li reports the use of E-vinylsilanes for the synthesis of dihydropyrans (ref 3a), Brimble reports that the Z-configuration of the vinylsilane is crucial for the formation of dihydropyrans: (b) Meilert, K.; Brimble, M. A. Org. Biolom. Chem. 2006, 4, 2184.
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31
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0025914098
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For the preparation of 10, see: (a) Majetich, G.; Song, J.-S.; Ringold, C.; Nemeth, G. A.; Newton, M. G. J. Org. Chem. 1991, 56, 3973.
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For the preparation of 10, see: (a) Majetich, G.; Song, J.-S.; Ringold, C.; Nemeth, G. A.; Newton, M. G. J. Org. Chem. 1991, 56, 3973.
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33
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0036354877
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For an alternative preparation of cyclohexenyl-fused pyrans, see
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For an alternative preparation of cyclohexenyl-fused pyrans, see: Loh, T.-P.; Feng, L.-C.; Yang, J.-Y. Synthesis 2002, 7, 937.
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34
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41149085525
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3N, THF), and iodide displacement (NaI, acetone, rt, 24 h).
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3N, THF), and iodide displacement (NaI, acetone, rt, 24 h).
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35
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41149142403
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2).
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2).
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38
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0141766891
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(c) Carreno, M. C.; Mazery, R. D.; Urbano, A.; Colobert, F.; Solladié, G. J. Org. Chem. 2003, 68, 7779.
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Solladié, G.5
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Marumoto, S.1
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Evans, P.A.1
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23944455842
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(f) Chandrasekhar, S.; Prakash, S. J.; Shyamsunder, T. Tetrahedron Lett. 2005, 46, 6651.
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Chandrasekhar, S.1
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4644228335
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Yu, W.; Mei, Y.; Kang, Y.; Hua, Z.; Jin, Z. Org. Lett. 2004, 6, 3217.
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44
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41149125472
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13C) for 13 were in complete accord with those reported for this compound by Clarke et al. (ref 20).
-
13C) for 13 were in complete accord with those reported for this compound by Clarke et al. (ref 20).
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