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1
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14644393617
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Preliminary communication: Clive, D. L. J.; Yu, M.; Li, Z. Chem. Commun. 2005, 906-908.
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Preliminary communication: Clive, D. L. J.; Yu, M.; Li, Z. Chem. Commun. 2005, 906-908.
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2
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0036929478
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Indolizidine and quinolizidine alkaloids: Michael, J. P. Nat. Prod. Rep. 2002, 19, 719-741.
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Indolizidine and quinolizidine alkaloids: Michael, J. P. Nat. Prod. Rep. 2002, 19, 719-741.
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-
-
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3
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22244454093
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For a recent new approach to quinolizidines, see
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For a recent new approach to quinolizidines, see: Maloney, K. M.; Danheiser, R. L. Org. Lett. 2005, 7, 3115-3118.
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Maloney, K.M.1
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4
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11144349848
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Pelletier, S. W, Ed, Pergamon: New York
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(a) Daly, J. W.; Garraffo, H. M.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: New York, 1999; Vol. 13, pp 1-161.
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Daly, J.W.1
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5
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0035232404
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Cordell, G. A, Ed, Academic Press: New York
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(b) Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2001; Vol. 55, pp 91-258.
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Michael, J.P.1
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6
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4344584930
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For a mechanistically related (and earlier) approach to the halichlorine system, see
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(a) For a mechanistically related (and earlier) approach to the halichlorine system, see: Christie, H. S.; Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12079-12084.
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(2004)
Proc. Natl. Acad. Sci. U.S.A
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Christie, H.S.1
Heathcock, C.H.2
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7
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29444435217
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A variant of our approach has been used in a formal synthesis of halichlorine: Andrade, R. B.; Martin, S. F. Org. Lett. 2005, 7, 5733-5735.
-
(b) A variant of our approach has been used in a formal synthesis of halichlorine: Andrade, R. B.; Martin, S. F. Org. Lett. 2005, 7, 5733-5735.
-
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8
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4744362831
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Reviews on the Morita-Baylis-Hillman reaction: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670.
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Reviews on the Morita-Baylis-Hillman reaction: (a) Drewes, S. E.; Roos, G. H. P. Tetrahedron 1988, 44, 4653-4670.
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9
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34547097579
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(b) Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8011-8062.
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Basavaiah, D.1
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10
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0000892247
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(c) Ciganek, E. Org. React. 1997, 51, 201-350.
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Org. React
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Ciganek, E.1
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11
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0037366617
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(d) Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891.
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Basavaiah, D.1
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Satyanarayana, T.3
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12
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0000532617
-
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For speculation on the mechanism of related intermolecular processes, see: Knochel, P.; Seebach, D. Tetrahedron Lett. 1981, 22, 3223-3226.
-
For speculation on the mechanism of related intermolecular processes, see: Knochel, P.; Seebach, D. Tetrahedron Lett. 1981, 22, 3223-3226.
-
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13
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0001403162
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Toujas, J.-L.; Jost, E.; Vaultier, M. Bull. Soc. Chim. Fr. 1997, 134, 713-717.
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Toujas, J.-L.1
Jost, E.2
Vaultier, M.3
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14
-
-
0028001763
-
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Pettit, G. R.; Singh, S. B.; Herald, D. L.; Lloyd-Williams, P.; Kantoci, D.; Burkett, D. D.; Barkóczy, J.; Hogan, F.; Wardlaw, T. R. J. Org. Chem. 1994, 59, 6287-6295.
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Burkett, D.D.6
Barkóczy, J.7
Hogan, F.8
Wardlaw, T.R.9
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15
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37049099292
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Cf.: Ansell, M. F.; Caton, M. P. L.; Stuttle, K. A. J. J. Chem. Soc., Perkin Trans. 1 1984, 1069-1077.
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Cf.: Ansell, M. F.; Caton, M. P. L.; Stuttle, K. A. J. J. Chem. Soc., Perkin Trans. 1 1984, 1069-1077.
-
-
-
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16
-
-
34547095822
-
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Cf.: Ikeda, M.; Shikaura, J.; Maekawa, N.; Daibuzono, K.; Teranishi, H.; Teraoka, Y.; Oda, N.; Ishibashi, H. Heterocycles 1999, 31-34.
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Cf.: Ikeda, M.; Shikaura, J.; Maekawa, N.; Daibuzono, K.; Teranishi, H.; Teraoka, Y.; Oda, N.; Ishibashi, H. Heterocycles 1999, 31-34.
-
-
-
-
17
-
-
34547122789
-
-
Racemic enol ethers: Calvet, A. P, Jacobelli, H, Junien, J.-L, Riviere, P, Roman, F. J. PCT Int. Appl. WO 9515948 A1, 1995
-
Racemic enol ethers: Calvet, A. P.; Jacobelli, H.; Junien, J.-L.; Riviere, P.; Roman, F. J. PCT Int. Appl. WO 9515948 A1, 1995.
-
-
-
-
18
-
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0033710022
-
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Balboni, G.; Marastoni, M.; Merighi, S.; Borea, P. A.; Tomatis, R. Eur. J. Med. Chem. 2000, 35, 979-988.
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Balboni, G.1
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19
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2442662859
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Cf, a
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33749096353
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(b) Ikeda, M.; Kugo, Y.; Sato, T. J. Chem. Soc., Perkin Trans. 1 1996, 1819-1824.
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Ikeda, M.1
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21
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34547115519
-
-
U.S. Patent 5,175,157
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Psiorz, M.; Heider, J.; Bomhard, A.; Reiffen, M.; Hauel, N.; Noll, K.; Narr, B.; Lillie, C.; Kobinger, W.; Dammgen, J. U.S. Patent 5,175,157, 1992.
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(1992)
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Psiorz, M.1
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Hauel, N.5
Noll, K.6
Narr, B.7
Lillie, C.8
Kobinger, W.9
Dammgen, J.10
-
22
-
-
0033530138
-
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Cf.: 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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Cf.: 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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24
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0035996258
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Sato, T.; Yamazaki, T.; Nakanishi, Y.; Uenishi, J.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 2002, 1438-1443.
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(2002)
J. Chem. Soc., Perkin Trans. 1
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-
Sato, T.1
Yamazaki, T.2
Nakanishi, Y.3
Uenishi, J.4
Ikeda, M.5
-
25
-
-
0037136380
-
-
Bustos, F.; Gorgojo, J. M.; Suero, R.; Aurrecoechea, J. M. Tetrahedron 2002, 58, 6837-6842.
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(2002)
Tetrahedron
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, pp. 6837-6842
-
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Bustos, F.1
Gorgojo, J.M.2
Suero, R.3
Aurrecoechea, J.M.4
-
26
-
-
34547101518
-
-
3 (M + Na) 278.17266, found 278.17267.
-
3 (M + Na) 278.17266, found 278.17267.
-
-
-
-
28
-
-
34547091985
-
-
Racemic ester 40 has been reported: Baldwin, J. J, McDonald, E, Moriarty, K. J, Sarko, C. R, Machinaga, N, Nakayama, A, Chiba, J, Iimura, S, Yoneda, Y. PCT Int. Appl. WO 2001000206 A1, 2001
-
(a) Racemic ester 40 has been reported: Baldwin, J. J.; McDonald, E.; Moriarty, K. J.; Sarko, C. R.; Machinaga, N.; Nakayama, A.; Chiba, J.; Iimura, S.; Yoneda, Y. PCT Int. Appl. WO 2001000206 A1, 2001.
-
-
-
-
29
-
-
33748731434
-
-
Optically pure ester: Lewis, A.; Wilkie, J.; Rutherford, T. J.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1998, 3777-3793.
-
(b) Optically pure ester: Lewis, A.; Wilkie, J.; Rutherford, T. J.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1998, 3777-3793.
-
-
-
-
30
-
-
0023930271
-
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Confalone, P. N.; Huie, E. M.; Ko, S. S.; Cole, G. M. J. Org. Chem. 1988, 53, 482-487.
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(1988)
J. Org. Chem
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Confalone, P.N.1
Huie, E.M.2
Ko, S.S.3
Cole, G.M.4
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31
-
-
37049076127
-
-
Cf.: Bode, M. L.; Kaye, P. T. J. Chem. Soc., Perkin Trans. 1 1993, 1809-1813.
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Cf.: Bode, M. L.; Kaye, P. T. J. Chem. Soc., Perkin Trans. 1 1993, 1809-1813.
-
-
-
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32
-
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2542448981
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E.g, a
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E.g.: (a) Cho, C.-W.; Kong, J.-R.; Krische, M. J. Org. Lett. 2004, 6, 1337-1339.
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(2004)
Org. Lett
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Cho, C.-W.1
Kong, J.-R.2
Krische, M.J.3
-
34
-
-
0028272243
-
-
N2′ displacement (analogous to 5 → 6) to form macrocycles, see: Bauchat, P.; Le Bras, N.; Rigal, L.; Foucaud, A. Tetrahedron 1994, 50, 7815-7826.
-
N2′ displacement (analogous to 5 → 6) to form macrocycles, see: Bauchat, P.; Le Bras, N.; Rigal, L.; Foucaud, A. Tetrahedron 1994, 50, 7815-7826.
-
-
-
-
35
-
-
0035937306
-
-
(d) Charette, A. B.; Janes, M. K.; Boezio, A. A. J. Org. Chem. 2001, 66, 2178-2180.
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(2001)
J. Org. Chem
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Charette, A.B.1
Janes, M.K.2
Boezio, A.A.3
-
36
-
-
0000183076
-
-
For synthons related to the acetates of MBH alcohols, see, for example: (i) Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211-5212 and references therein,
-
(e) For synthons related to the acetates of MBH alcohols, see, for example: (i) Brocchini, S. J.; Eberle, M.; Lawton, R. G. J. Am. Chem. Soc. 1988, 110, 5211-5212 and references therein,
-
-
-
-
39
-
-
0037029826
-
-
For examples of closure onto an ester: (a) Basavaiah, D, Reddy, R. M, Kumaragurubaran, N, Sharada, D. S. Tetrahedron 2002, 58, 3693-3697
-
For examples of closure onto an ester: (a) Basavaiah, D.; Reddy, R. M.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron 2002, 58, 3693-3697.
-
-
-
-
40
-
-
0032495082
-
-
Cf.: Familoni, O. B.; Kaye, P. T.; Klaas, P. J. Chem. Commun. 1998, 2563-2564.
-
(b) Cf.: Familoni, O. B.; Kaye, P. T.; Klaas, P. J. Chem. Commun. 1998, 2563-2564.
-
-
-
-
41
-
-
0042575704
-
-
For a related case, where such closure onto an ester does not occur
-
(c) For a related case, where such closure onto an ester does not occur: O'Dell, D. K.; Nicholas, K. M. J. Org. Chem. 2003, 68, 6427-6430.
-
(2003)
J. Org. Chem
, vol.68
, pp. 6427-6430
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O'Dell, D.K.1
Nicholas, K.M.2
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43
-
-
0001302368
-
-
Auvray, P.; Knochel, P.; Normant, J. F. Tetrahedron 1988, 44, 6095-6106.
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(1988)
Tetrahedron
, vol.44
, pp. 6095-6106
-
-
Auvray, P.1
Knochel, P.2
Normant, J.F.3
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44
-
-
0037423248
-
-
Aggarwal, V. K.; Emme, I.; Fulford, S. Y. J. Org. Chem. 2003, 68, 692-700.
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(2003)
J. Org. Chem
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, pp. 692-700
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Aggarwal, V.K.1
Emme, I.2
Fulford, S.Y.3
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46
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49349139760
-
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Review: b
-
Review: (b) Clive, D. L. J. Tetrahedron 1978, 34, 1049-1132.
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(1978)
Tetrahedron
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, pp. 1049-1132
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Clive, D.L.J.1
-
48
-
-
0001126437
-
-
Seebach, D.; Calderari, G.; Knochel, P. Tetrahedron 1985, 41, 4861-4872.
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(1985)
Tetrahedron
, vol.41
, pp. 4861-4872
-
-
Seebach, D.1
Calderari, G.2
Knochel, P.3
-
49
-
-
0034693340
-
-
Mase, N.; Watanabe, Y.; Toru, T.; Kakumoto, T.; Hagiwara, T. J. Org. Chem. 2000, 65, 7083-7090.
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(2000)
J. Org. Chem
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, pp. 7083-7090
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-
Mase, N.1
Watanabe, Y.2
Toru, T.3
Kakumoto, T.4
Hagiwara, T.5
-
51
-
-
0000014261
-
-
(b) Guindon, Y.; Faucher, A.-M.; Bourque, E.; Caron, V.; Jung, G.; Landry, S. R. J. Org. Chem. 1997, 62, 9276-9283.
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(1997)
J. Org. Chem
, vol.62
, pp. 9276-9283
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Guindon, Y.1
Faucher, A.-M.2
Bourque, E.3
Caron, V.4
Jung, G.5
Landry, S.R.6
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52
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-
33747081937
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-
(a) Sheng, S.-R.; Wang, Q.; Wang, Q.-Y.; Guo, L.; Hunag, X. Synlett 2006, 1887-1890.
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(2006)
Synlett
, pp. 1887-1890
-
-
Sheng, S.-R.1
Wang, Q.2
Wang, Q.-Y.3
Guo, L.4
Hunag, X.5
-
53
-
-
25444466534
-
-
(b) Shiina, I.; Yamai, Y.; Shimazaki, T. J. Org. Chem. 2005, 70, 8103-8106.
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(2005)
J. Org. Chem
, vol.70
, pp. 8103-8106
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Shiina, I.1
Yamai, Y.2
Shimazaki, T.3
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54
-
-
23844546658
-
-
(a) Cases, M.; de Turiso, F. G.-L.; Hadjisoteriou, M. S.; Pattenden, G. Org. Biomol. Chem. 2005, 3, 2786-2804.
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(2005)
Org. Biomol. Chem
, vol.3
, pp. 2786-2804
-
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Cases, M.1
de Turiso, F.G.-L.2
Hadjisoteriou, M.S.3
Pattenden, G.4
-
58
-
-
0345254963
-
-
(b) Ramachandran, P. V.; Rudd, M. T.; Burghardt, T. E.; Reddy, M. V. R. J. Org. Chem. 2003, 68, 9310-9316.
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(2003)
J. Org. Chem
, vol.68
, pp. 9310-9316
-
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Ramachandran, P.V.1
Rudd, M.T.2
Burghardt, T.E.3
Reddy, M.V.R.4
-
59
-
-
0001367039
-
-
(c) Tsuda, T.; Yoshida, T.; Saegusa, T. J. Org. Chem. 1988, 53, 1037-1040.
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(1988)
J. Org. Chem
, vol.53
, pp. 1037-1040
-
-
Tsuda, T.1
Yoshida, T.2
Saegusa, T.3
-
60
-
-
0034665413
-
-
Corresponding ethyl ester: Lebarillier, L.; Outurquin, F.; Paulmier, C. Tetrahedron 2000, 56, 7483-7493.
-
Corresponding ethyl ester: Lebarillier, L.; Outurquin, F.; Paulmier, C. Tetrahedron 2000, 56, 7483-7493.
-
-
-
-
61
-
-
0026674211
-
-
Cf.: Holmes, A. B.; Nadin, A.; O'Hanlon, P. J.; Pearson, N. D. Tetrahedron: Asymmetry 1992, 3, 1289-1302.
-
Cf.: Holmes, A. B.; Nadin, A.; O'Hanlon, P. J.; Pearson, N. D. Tetrahedron: Asymmetry 1992, 3, 1289-1302.
-
-
-
-
64
-
-
0026086216
-
-
Cf, a
-
Cf.: (a) Simpkins, N. S. Tetrahedron 1991, 47, 323-332.
-
(1991)
Tetrahedron
, vol.47
, pp. 323-332
-
-
Simpkins, N.S.1
-
66
-
-
0035952979
-
-
23.5D -4.02 (c 2.12, EtOH).
-
23.5D -4.02 (c 2.12, EtOH).
-
-
-
-
67
-
-
0035968411
-
-
25D -10.1 (c 1.88, EtOH).
-
25D -10.1 (c 1.88, EtOH).
-
-
-
-
68
-
-
0042865048
-
-
23D -10.1 (c 1.8, EtOH).
-
23D -10.1 (c 1.8, EtOH).
-
-
-
-
69
-
-
0025168551
-
-
27D -10.8 (c 1.76, EtOH).
-
27D -10.8 (c 1.76, EtOH).
-
-
-
-
70
-
-
0033588329
-
-
26D -10.8 (c 1.76 EtOH).
-
26D -10.8 (c 1.76 EtOH).
-
-
-
-
71
-
-
0001156020
-
-
23D -7.9 (c 0.15, EtOH).
-
23D -7.9 (c 0.15, EtOH).
-
-
-
-
72
-
-
33749089348
-
-
22D -7.9 (c 0.15, EtOH).
-
22D -7.9 (c 0.15, EtOH).
-
-
-
-
73
-
-
0012862243
-
-
23D -10.2 (c 1.76, EtOH).
-
23D -10.2 (c 1.76, EtOH).
-
-
-
-
74
-
-
0002475948
-
-
25D -20.5 (c 0.98, EtOH).
-
25D -20.5 (c 0.98, EtOH).
-
-
-
-
75
-
-
0033794226
-
-
25D -20.5 (c 0.98, EtOH).
-
25D -20.5 (c 0.98, EtOH).
-
-
-
|