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1
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33646268052
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note
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According to a Beilstein search; for some examples see references 2-7.
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2
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4644225378
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Hermet, J.-P. R.; McGrath, M. J.; O'Brien, P.; Porter, D. W.; Gilday, J. Chem. Commun. 2004, 1830.
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Hermet, J.-P.R.1
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Gilday, J.5
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3
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0025003933
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(a) Morley, C.; Knight, D. W.; Share, A. C. Tetrahedron: Asymmetry 1990, 1, 147.
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Tetrahedron: Asymmetry
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Morley, C.1
Knight, D.W.2
Share, A.C.3
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4
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0035817296
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(b) Ledoux, S.; Marchalant, E.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 5397.
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Tetrahedron Lett.
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Ledoux, S.1
Marchalant, E.2
Célérier, J.-P.3
Lhommet, G.4
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Back, T. G.; Hamilton, M. D.; Lim, V. J. J.; Parvez, M. J. Org. Chem. 2005, 70, 967.
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Lim, V.J.J.3
Parvez, M.4
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Barilli, A.; Belinghieri, F.; Passarella, D.; Lesma, G.; Riva, S.; Silvani, A.; Danieli, B. Tetrahedron: Asymmetry 2004, 15, 2921.
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Tetrahedron: Asymmetry
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Barilli, A.1
Belinghieri, F.2
Passarella, D.3
Lesma, G.4
Riva, S.5
Silvani, A.6
Danieli, B.7
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7
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0344391929
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Angoli, M.; Barilli, A.; Lesma, G.; Passarella, D.; Riva, S.; Silvani, A.; Danieli, B. J. Org. Chem. 2003, 68, 9525.
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J. Org. Chem.
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Angoli, M.1
Barilli, A.2
Lesma, G.3
Passarella, D.4
Riva, S.5
Silvani, A.6
Danieli, B.7
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8
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0037030654
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(a) Danilewicz, J. C.; Abel, S. M.; Brown, A. D.; Fish, P. V.; Hawkeswood, E.; Holland, S. J.; James, K.; McElroy, A. B.; Overington, J.; Powling, M. J.; Rance, D. J. J. Med. Chem. 2002, 45, 2432.
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Danilewicz, J.C.1
Abel, S.M.2
Brown, A.D.3
Fish, P.V.4
Hawkeswood, E.5
Holland, S.J.6
James, K.7
McElroy, A.B.8
Overington, J.9
Powling, M.J.10
Rance, D.J.11
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9
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0033026387
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(b) Katori, M.; Tamaki, T.; Tanaka, M.; Konoeda, Y.; Yokota, N.; Hayashi, T.; Uchida, Y.; Hui, Y.; Takahashi, Y.; Kakita, A.; Kawamura, A. Transplant. Proc. 1999, 31, 1016.
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Katori, M.1
Tamaki, T.2
Tanaka, M.3
Konoeda, Y.4
Yokota, N.5
Hayashi, T.6
Uchida, Y.7
Hui, Y.8
Takahashi, Y.9
Kakita, A.10
Kawamura, A.11
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10
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33646262465
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PCT Int. Appl. WO 2004092164, 2004
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(c) Groneberg, R. D.; Zhan, J.; Askew, B.; D'Amico, D.; Han, N.; Fotsch, C. H.; Liu, Q.; Riahi, B.; Zhu, J.; Yang, K.; Chen, J. J.; Nomak, R. PCT Int. Appl. WO 2004092164, 2004.
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Groneberg, R.D.1
Zhan, J.2
Askew, B.3
D'Amico, D.4
Han, N.5
Fotsch, C.H.6
Liu, Q.7
Riahi, B.8
Zhu, J.9
Yang, K.10
Chen, J.J.11
Nomak, R.12
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11
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0033579646
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Ledoux, S.; Célérier, J.-P.; Lhommet, G. Tetrahedron Lett. 1999, 40, 9019.
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Tetrahedron Lett.
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Ledoux, S.1
Célérier, J.-P.2
Lhommet, G.3
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12
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0037471537
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(a) Chippindale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253.
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Chippindale, A.M.1
Davies, S.G.2
Iwamoto, K.3
Parkin, R.M.4
Smethurst, C.A.P.5
Smith, A.D.6
Rodriguez-Solla, H.7
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13
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(b) Davies, S. G.; Iwamoto, K.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Synlett 2002, 1146.
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Synlett
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Davies, S.G.1
Iwamoto, K.2
Smethurst, C.A.P.3
Smith, A.D.4
Rodriguez-Solla, H.5
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15
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(a) Wanner, K. T.; Kärtner, A. Arch. Pharm. (Weinheim, Ger.) 1987, 320, 1253.
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Arch. Pharm. (Weinheim, Ger.)
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Kärtner, A.2
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(c) Matsumura, Y.; Kanda, Y.; Shirai, K.; Onomura, O.; Maki, T. Tetrahedron 2000, 56, 7411.
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Matsumura, Y.1
Kanda, Y.2
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Onomura, O.4
Maki, T.5
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18
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(a) Calvet, S.; David, O.; Vanucci-Bacqué, C.; Fargeau-Bellassoued, M.-C.; Lhommet, G. Tetrahedron 2003, 59, 6333.
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Calvet, S.1
David, O.2
Vanucci-Bacqué, C.3
Fargeau-Bellassoued, M.-C.4
Lhommet, G.5
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19
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1842638269
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(b) David, O.; Calvet, S.; Chau, F.; Vanucci-Bacqué, C.; Fargeau-Bellassoued, M.-C.; Lhommet, G. J. Org. Chem. 2004, 69, 2888.
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David, O.1
Calvet, S.2
Chau, F.3
Vanucci-Bacqué, C.4
Fargeau-Bellassoued, M.-C.5
Lhommet, G.6
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20
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10844275418
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(c) Pousset, C.; Callens, R.; Marinetti, A.; Larchevêque, M. Synlett 2004, 2766.
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Synlett
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Pousset, C.1
Callens, R.2
Marinetti, A.3
Larchevêque, M.4
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21
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3042825147
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(a) Gray, D.; Concellon, C.; Gallagher, T. J. Org. Chem. 2004, 69, 4849.
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Gray, D.1
Concellon, C.2
Gallagher, T.3
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22
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0033530138
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(b) DeVita, R. J.; Goulet, M. T.; Wyvratt, M. J.; Fisher, M. H.; Lo, J.-L.; Yang, Y. T.; Cheng, K.; Smith, R. G. Bioorg. Med. Chem. Lett. 1999, 9, 2621.
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DeVita, R.J.1
Goulet, M.T.2
Wyvratt, M.J.3
Fisher, M.H.4
Lo, J.-L.5
Yang, Y.T.6
Cheng, K.7
Smith, R.G.8
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23
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7444224237
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(a) Pousset, C.; Callens, R.; Haddad, M.; Larchevêque, M. Tetrahedron: Asymmetry 2004, 15, 3407.
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Tetrahedron: Asymmetry
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Pousset, C.1
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Haddad, M.3
Larchevêque, M.4
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24
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0033386828
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(b) Chung, H.-k.; Kim, H.-w.; Chung, K.-H. Heterocycles 1999, 51, 2983.
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Heterocycles
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Chung, H.-K.1
Kim, H.-W.2
Chung, K.-H.3
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25
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0029004264
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For some examples of enantioselective Michael additions of lithiated derivatives of 4 to α,β-unsaturated esters, see: (a) Davies, S. G.; Fenwick, D. R. J. Chem. Soc., Chem. Commun. 1995, 1109.
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(1995)
J. Chem. Soc., Chem. Commun.
, pp. 1109
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Davies, S.G.1
Fenwick, D.R.2
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27
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0037013920
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(c) Bull, S. D.; Davies, S. G.; Roberts, P. M.; Savory, E. D.; Smith, A. D. Tetrahedron 2002, 58, 4629.
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(2002)
Tetrahedron
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Bull, S.D.1
Davies, S.G.2
Roberts, P.M.3
Savory, E.D.4
Smith, A.D.5
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28
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33646270766
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note
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(d) Ref. 9a.
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29
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0034595783
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For related approaches to the corresponding ethyl and tert-butyl esters, see ref. 2 and the following: Baenziger, M.; Gobbi, L.; Riss, B. P.; Schaefer, F.; Vaupel, A. Tetrahedron: Asymmetry 2000, 11, 2231.
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(2000)
Tetrahedron: Asymmetry
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-
Gobbi, L.1
Riss, B.P.2
Schaefer, F.3
Vaupel, A.4
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30
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33646229681
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note
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In the presence of two equivalents of (5)-4 and no additional base, compound 5 was obtained in a slightly improved yield (86%), but with a decreased diastereomeric ratio (67:33).
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31
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33646260813
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note
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The analogous cyclization of the tosyloxy derivative of 3 gave comparable results; nevertheless this route was less efficient - the tosyl derivative was prepared in a lower yield (73% from 2).
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32
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33646264191
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note
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For a related cyclization of an ω-iodo enoate, see ref. 2.
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33
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0028808860
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Tsukada, N.; Shimada, T.; Gyoung, Y. S.; Asao, N.; Yamamoto, Y. J. Org. Chem. 1995, 60, 143.
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J. Org. Chem.
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, pp. 143
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Tsukada, N.1
Shimada, T.2
Gyoung, Y.S.3
Asao, N.4
Yamamoto, Y.5
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34
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33646237703
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note
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Mesylate (E)-3 was synthesized from (E)-2, which was accessible by distillation of (E/Z)-2, see ref. 23.
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-
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35
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33646271020
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note
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The crude product can also be purified by distillation (bp 75-85 °C, 0.02 mbar) through a Vigreux column (10 cm). Even though the lower boiling fractions were enriched with the minor diastereomer (S.S)-5, satisfactory separation of the two diastereomers was not achieved.
-
-
-
-
36
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33646269622
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note
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There is just a short filtration through a pad of silica gel prior to the fractional crystallization.
-
-
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37
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33646266629
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note
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All fractions boiling below 70 °C/0.1 mbar were discarded: fractions boiling at 71-75 °C/0. 1 mbar contained mainly (Z)-2, fractions boiling at 92-96 °C/0. 1 mbar provided pure (E)-2.
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38
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0029070308
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Craig, D.; Geach, N. J.; Pearson, C. J.; Slawin, A. M. Z.; White, A. J. P.; Williams, D. J. Tetrahedron 1995, 51, 6071.
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(1995)
Tetrahedron
, vol.51
, pp. 6071
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Craig, D.1
Geach, N.J.2
Pearson, C.J.3
Slawin, A.M.Z.4
White, A.J.P.5
Williams, D.J.6
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