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1
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2242483151
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U.S. Patent 5,455,348, Oct 2, 1995
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(a) Austel, V.; Eisert, W.; Himmelsbach, F.; Linz, G.; Mueller, T.; Pieper, H.; Welsenberger, J. U.S. Patent 5,455,348, Oct 2, 1995.
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Austel, V.1
Eisert, W.2
Himmelsbach, F.3
Linz, G.4
Mueller, T.5
Pieper, H.6
Welsenberger, J.7
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2
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2242477769
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U.S. Patent 5,591,769, Jan 7, 1997
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(b) Himmelsbach, F.; Austel, V.; Pieper, H.; Eisert, W.; Mueller, T.; Weisenberger, J.; Linz, G.; Krueger, G. U.S. Patent 5,591,769, Jan 7, 1997.
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Himmelsbach, F.1
Austel, V.2
Pieper, H.3
Eisert, W.4
Mueller, T.5
Weisenberger, J.6
Linz, G.7
Krueger, G.8
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3
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2242483996
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note
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tert-Butyl ester functionality was specifically chosen for the crystallinity of the intermediates in the synthesis.
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4
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2242464219
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note
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The trans/cis stereochemical notation refers to the C3 and C5 positions.
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5
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33845376014
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(a) Thottathil, J. K.; Moniot, J. L.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem. 1986, 51, 3140.
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Thottathil, J.K.1
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Kissick, T.P.5
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(c) Brena-Valle, L. J.; Sanchez, R. C.; Cruz-Almanza, R. Tetrahedron: Asymmetry 1996, 7, 1019.
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(e) Baldwin, J. E.; Miranda, T.; Moloney, M. Tetrahedron 1989, 45, 7459.
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Baldwin, J.E.1
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Hon, Y.-S.1
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13
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0027301896
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(i) Ezquerra, J.; Pedregal, C.; Rubio, A.; Yruretagoyena, B.; Escribano, A.; Sanchez-Ferrando, F. Tetrahedron 1993, 49, 8665.
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Ezquerra, J.1
Pedregal, C.2
Rubio, A.3
Yruretagoyena, B.4
Escribano, A.5
Sanchez-Ferrando, F.6
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(l) Baldwin, J. E.; Moloney, M. G.; Shim, S. B. Tetrahedron Lett. 1991, 32, 1379.
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Baldwin, J.E.1
Moloney, M.G.2
Shim, S.B.3
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18
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0030066579
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(a) Beard, M. J.; Bailey, J. H.; Cherry, D. T.; Moloney, M. G.; Shim, S. B.; Statham, K. A. Tetrahedron 1996, 52, 3719.
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Beard, M.J.1
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Statham, K.A.6
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19
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0028897506
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(b) Bamford, M. J.; Beard, M.; Cherry, D. T.; Moloney, M. G. Tetrahedron: Asymmetry 1995, 6, 337.
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, vol.6
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Bamford, M.J.1
Beard, M.2
Cherry, D.T.3
Moloney, M.G.4
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20
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2242437417
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note
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Acetal 5b is too labile under decarboxylation conditions. For 5c and 5d, isobutyraldehyde (bp 63 °C) and pivalaldehyde (bp 74 °C) can be conveniently removed by evaporation either in protection or deprotection steps, but they are more difficult to deprotect under mild conditions.
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21
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84987590301
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(a) Ackermann, J.; Matthes, M.; Tamm, C. Helv. Chim. Acta 1990, 73, 122.
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Ackermann, J.1
Matthes, M.2
Tamm, C.3
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22
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0025014988
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(b) Attwood, M. R.; Carr, M. G.; Jordan, S. Tetrahedron Lett. 1990, 31, 283.
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Attwood, M.R.1
Carr, M.G.2
Jordan, S.3
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23
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85004559891
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(c) Tanaka, K.; Yoshifuji, S.; Nitta, Y. Chem. Pharm. Bull. 1986, 34, 3879.
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(1986)
Chem. Pharm. Bull.
, vol.34
, pp. 3879
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Tanaka, K.1
Yoshifuji, S.2
Nitta, Y.3
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25
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2242489369
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(b) Bernard, A. M.; Cerioni, G.; Piras, P. P.; Seu, G. Synthesis 1990, 871.
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(1990)
Synthesis
, pp. 871
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Bernard, A.M.1
Cerioni, G.2
Piras, P.P.3
Seu, G.4
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27
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2242423853
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note
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1H NMR integration in which the C-4 protons are characteristic for the trans isomer (δ 3.41 ppm) and the cis isomer (δ 3.59 ppm).
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28
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0026001407
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Hamada, Y.; Hara, O.; Kawai, A.; Kohno, Y.; Shioiri, T. Tetrahedron 1991, 47, 8635.
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(1991)
Tetrahedron
, vol.47
, pp. 8635
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Hamada, Y.1
Hara, O.2
Kawai, A.3
Kohno, Y.4
Shioiri, T.5
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29
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2242450815
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note
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The C-O bond was cleaved and the corresponding N-benzyl product was obtained.
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32
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2242478684
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note
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1H NMR spectrum of crude 11 revealed that ∼5% starting material 10 remained intact as well as some unidentified side-products.
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33
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2242456167
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note
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1H NMR of the corresponding Mosher ester of 11 derived from both (5S)- and (5R)-2.
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34
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0032559310
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For general procedures, see: Yee, N. K.; Nummy, L. J.; Byrne, D. P.; Smith, L. L.; Roth, G. P. J. Org. Chem. 1998, 63, 326
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(1998)
J. Org. Chem.
, vol.63
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Yee, N.K.1
Nummy, L.J.2
Byrne, D.P.3
Smith, L.L.4
Roth, G.P.5
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