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1
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Maslen, S.L.31
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0000893313
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3
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37049066358
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For a radical cyclization-atom transfer-radical cyclization sequence related to that encountered in this work, see: Clive, D. L. J.; Khodabocus, A.; Cantin, M.; Tao, Y. J. Chem. Soc., Chem. Commun. 1991, 1755-1757.
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4
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0033610461
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6
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0029278842
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7
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0027140526
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8
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2342524627
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33750040568
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For a preliminary account of work shown in Schemes 1 and 2, see
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11
-
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70449684555
-
-
note
-
3SnH were 10 and 100 mM, respectively (see the Supporting Information for details of the cyclizations shown in Schemes 1 and 2).
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-
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15
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84918717463
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Van Bekkum, H.; Van Den Bosch, C.; Van Minnenpathuis, G.; DeMos, J. C.; van Wijk, A. M. Recueil 1971, 90, 137-149.
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22
-
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70449680694
-
-
note
-
Compounds 26 and 27 were characterized as a mixture. Manipulation of this mixture provided compounds 26 (free of 27) as a mixture (see the Supporting Information for details).
-
-
-
-
23
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0004694395
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84986412670
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26
-
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70449649142
-
-
note
-
Omission of theK2CO3 (acid sponge) resulted in formation of a large number of products.
-
-
-
-
27
-
-
70449647607
-
-
note
-
Alcohol 40 was sensitive and was used in the subsequent free-radical cyclization on the same day it was prepared.
-
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29
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0000776391
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84984088671
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32
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0000123060
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For an analogous isomerization-desilylation, see
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For an analogous isomerization-desilylation, see: Paquette, L. A.; Wells, G. J.; Horn, K. A.; Yan, T.-H. Tetrahedron Lett. 1982, 23, 263-266.
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33
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0000163018
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Hart, D.J.1
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36
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37049104091
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For other relevant cyclizations, see
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For other relevant cyclizations, see: Roumestant, M. L.; Arseniyadis, S.; Gore, J.; Laurent, A. J. Chem. Soc., Chem. Commun. 1976, 479-480.
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38
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64349122718
-
-
It is also possible that the slow rate at which allylic radicals undergo hydrogen atom transfer may also contribute to the success of this strategy. For some relevant references, see
-
It is also possible that the slow rate at which allylic radicals undergo hydrogen atom transfer may also contribute to the success of this strategy. For some relevant references, see: Hayes, C. J.; Burgess, D. R. Jr. J. Phys. Chem.A2009, 113, 2473-2482.
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41
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37049145470
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For strain in bicyclo[3.3.0]octanes, see
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For strain in bicyclo[3.3.0]octanes, see: Barrett, J. W.; Linstead, R. P. J. Chem. Soc. 1935, 436-442.
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70449677071
-
-
note
-
Tri-n-butyltin hydride mediated cyclization of 7-epi-49 provided 7-epi-52 (mp 101-105 °C) in 63% yield. The structure of this compound was established by X-ray crystallography.
-
-
-
-
44
-
-
84980127075
-
-
Prepared from commercially available chloromethyl pivalate using a Finkelstein reaction (36 mmol of chloromethyl pivalate and 54 mmol of sodium iodide in 40mL of acetone at roomtemperature for 12 h) and used within 24 h
-
Prepared from commercially available chloromethyl pivalate using a Finkelstein reaction (36 mmol of chloromethyl pivalate and 54 mmol of sodium iodide in 40mL of acetone at roomtemperature for 12 h) and used within 24 h: Finkelstein, H. Chem. Ber. 1910, 43, 1528-1532.
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Finkelstein, H.1
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