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(c) Luesch H., Yoshida W.Y., Moore R.E., Paul V.J., Mooberry S.L. J. Nat. Prod. 63:2000;611-615.
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Luesch, H.1
Yoshida, W.Y.2
Moore, R.E.3
Paul, V.J.4
Mooberry, S.L.5
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6
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0032572865
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For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a) Winter E., Hoppe D. Tetrahedron. 54:1998;10329-10338 (b) Maezaki N., Matsumori Y., Shogaki T., Soejima M., Ohishi H., Tanaka T., Iwata C. Tetrahedron. 54:1998;13087-13104. (c) For a synthesis of (+)-1: Kogure T., Eliel E.L. J. Org. Chem. 49:1984;576-579.
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(1998)
Tetrahedron
, vol.54
, pp. 10329-10338
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Winter, E.1
Hoppe, D.2
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7
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0032558597
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-
For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a) Winter E., Hoppe D. Tetrahedron. 54:1998;10329-10338 (b) Maezaki N., Matsumori Y., Shogaki T., Soejima M., Ohishi H., Tanaka T., Iwata C. Tetrahedron. 54:1998;13087-13104. (c) For a synthesis of (+)-1: Kogure T., Eliel E.L. J. Org. Chem. 49:1984;576-579.
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(1998)
Tetrahedron
, vol.54
, pp. 13087-13104
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Maezaki, N.1
Matsumori, Y.2
Shogaki, T.3
Soejima, M.4
Ohishi, H.5
Tanaka, T.6
Iwata, C.7
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8
-
-
0021261945
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For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a). (c) For a synthesis of (+)-1:
-
For two recent syntheses of (-)-1 with a comprehensive account of previous work: (a) Winter E., Hoppe D. Tetrahedron. 54:1998;10329-10338 (b) Maezaki N., Matsumori Y., Shogaki T., Soejima M., Ohishi H., Tanaka T., Iwata C. Tetrahedron. 54:1998;13087-13104. (c) For a synthesis of (+)-1: Kogure T., Eliel E.L. J. Org. Chem. 49:1984;576-579.
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J. Org. Chem.
, vol.49
, pp. 576-579
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Kogure, T.1
Eliel, E.L.2
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9
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0342699502
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For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
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(2000)
Tetrahedron Lett.
, vol.41
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Kanada, R.M.1
Taniguchi, T.2
Ogasawara, K.3
-
10
-
-
0034715457
-
-
For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
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J. Am. Chem. Soc.
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, pp. 10470-10471
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Wan, Z.H.1
Nelson, S.G.2
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11
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0034649735
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-
For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
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Org. Lett.
, pp. 4013-4015
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Trost, B.M.1
Tang, W.P.2
Schulte, J.L.3
-
12
-
-
0034987510
-
-
For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
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(2001)
J. Chem. Soc., Perkin Trans. 1
, pp. 645-653
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Date, M.1
Tamai, Y.2
Hattori, T.3
Takayama, H.4
Kamikubo, Y.5
Miyano, S.6
-
13
-
-
0035979046
-
-
For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
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(2001)
Org. Lett.
, pp. 1741-1744
-
-
Suzuki, T.1
Ohmori, K.2
Suzuki, K.3
-
14
-
-
0035801883
-
-
For more recent syntheses of (-)-1, see: (a) Kanada, R.M.; Taniguchi, T.; Ogasawara, K. Tetrahedron Lett. 2000, 41, 3631-3635. (b) Wan. Z.H.; Nelson, S.G. J. Am. Chem. Soc. 2000, 122, 10470-10471. (c) Trost, B.M.; Tang, W.P.; Schulte, J.L. Org. Lett. 2000, 4013-4015. (d) Date, M.; Tamai, Y.; Hattori, T.; Takayama, H.; Kamikubo, Y.; Miyano S. J. Chem. Soc., Perkin Trans. 1 2001, 645-653. (e) Suzuki, T.; Ohmori, K.; Suzuki, K. Org. Lett. 2001, 1741-1744. (f) Ghosh, A.K.; Shirai, M. Tetrahedron Lett. 2001, 42, 6231-6233.
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(2001)
Tetrahedron Lett.
, vol.42
, pp. 6231-6233
-
-
Ghosh, A.K.1
Shirai, M.2
-
15
-
-
0033913361
-
-
For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
-
(2000)
Synlett
, pp. 1019-1021
-
-
Kanada, R.M.1
Taniguchi, T.2
Ogasawara, K.3
-
16
-
-
0037013913
-
-
For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 4175-4178
-
-
Tanaka, H.1
Kozuki, Y.2
Ogasawara, K.3
-
17
-
-
0036320960
-
-
For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
-
(2002)
Synth. Commun.
, vol.32
, pp. 2187-2194
-
-
Zhang, R.Z.1
Wang, Z.Q.2
Wei, F.P.3
Huang, Y.R.4
-
18
-
-
0035544148
-
-
For syntheses of (+)-2, see: (a). For syntheses of (±)-2, see: (c). A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b
-
For syntheses of (+)-2, see: (a) Kanada R.M., Taniguchi T., Ogasawara K. Synlett. 2000;1019-1021 (b) Tanaka H., Kozuki Y., Ogasawara K. Tetrahedron Lett. 43:2002;4175-4178. For syntheses of (±)-2, see: (c) Zhang R.Z., Wang Z.Q., Wei F.P., Huang Y.R. Synth. Commun. 32:2002;2187-2194 (d) Krauss J. Nat. Prod. Lett. 15:2001;393-399. A synthesis of the unnatural enantiomer of tanikolide, (-)-2, is described in the supplementary information of Ref. 3b.
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(2001)
Nat. Prod. Lett.
, vol.15
, pp. 393-399
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Krauss, J.1
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Carda M., Castillo E., Rodríguez S., Uriel S., Marco J.A. Synlett. 1999;1639-1641.
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Castillo, E.2
Rodríguez, S.3
Uriel, S.4
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Carda, M.2
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Castillo, E.5
Murga, J.6
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(a) Marco J.A., Carda M., González F., Rodríguez S., Murga J. Liebigs Ann. Chem. 1996;1801-1810 (b) Carda M., Rodríguez S., Murga J., Falomir E., Marco J.A., Röper H. Synth. Commun. 29:1999;2601-2610.
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Carda, M.2
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Rodríguez, S.4
Murga, J.5
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23
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(a) Marco J.A., Carda M., González F., Rodríguez S., Murga J. Liebigs Ann. Chem. 1996;1801-1810 (b) Carda M., Rodríguez S., Murga J., Falomir E., Marco J.A., Röper H. Synth. Commun. 29:1999;2601-2610.
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Carda, M.1
Rodríguez, S.2
Murga, J.3
Falomir, E.4
Marco, J.A.5
Röper, H.6
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24
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0001116226
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and references cited therein
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Carda M., Castillo E., Rodríguez S., González F., Marco J.A. Tetrahedron: Asymmetry. 12:2001;1417-1429. and references cited therein.
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Tetrahedron: Asymmetry
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Carda, M.1
Castillo, E.2
Rodríguez, S.3
González, F.4
Marco, J.A.5
-
25
-
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0012875586
-
-
note
-
The stereostructure of tosylate 5 has been further secured with the aid of an X-ray diffraction analysis. Crystallographic data (excluding structure factors) have been deposited at the Cambridge Crystallographic Data Center as supplementary material with reference CCDC-195658. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
-
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26
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0000220284
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(a) Lipshutz B.H., Sengupta S. Org. React. 41:1992;135-631 (b) Krause N. Modern Organocopper Chemistry. 2002;Wiley/VCH, Weinheim.
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Lipshutz, B.H.1
Sengupta, S.2
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0004246896
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N. Krause. Weinheim: Wiley/VCH
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(a) Lipshutz B.H., Sengupta S. Org. React. 41:1992;135-631 (b) Krause N. Modern Organocopper Chemistry. 2002;Wiley/VCH, Weinheim.
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Modern Organocopper Chemistry
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0344006321
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(a) Fürstner A. Angew. Chem. Int. Ed. 39:2000;3012-3043 (b) Trnka T., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
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Angew. Chem. Int. Ed.
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Fürstner, A.1
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29
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0034746687
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(a) Fürstner A. Angew. Chem. Int. Ed. 39:2000;3012-3043 (b) Trnka T., Grubbs R.H. Acc. Chem. Res. 34:2001;18-29.
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Acc. Chem. Res.
, vol.34
, pp. 18-29
-
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Trnka, T.1
Grubbs, R.H.2
-
30
-
-
0012815294
-
-
note
-
This oxidation also produced small amounts (10-15%) of the oxygenation product (a cyclic ketone) at the alternative allylic position.
-
-
-
-
31
-
-
0036245934
-
-
Attempts at preparing lactone 10 in a more direct way by RCM of the methacrylate of alcohol 7 with the standard ruthenium catalyst were unsuccessful (see Ref. 6). Very recently, a lactone with a conjugated trisubstituted C=C bond has been prepared by means of RCM with the aid of a second-generation ruthenium catalyst: (a) Cossy J., Bauer D., Bellosta V. Synlett. 2002;715-718. However, the unsatisfactory yield in the preparation of the aforementioned methacrylate led us to disregard this alternative. See, however: (b) Rodríguez S., Castillo E., Carda M., Marco J.A. Tetrahedron. 58:2002;1185-1192.
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(2002)
Synlett
, pp. 715-718
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Cossy, J.1
Bauer, D.2
Bellosta, V.3
-
32
-
-
0037016933
-
-
Attempts at preparing lactone 10 in a more direct way by RCM of the methacrylate of alcohol 7 with the standard ruthenium catalyst were unsuccessful (see Ref. 6). Very recently, a lactone with a conjugated trisubstituted C=C bond has been prepared by means of RCM with the aid of a second-generation ruthenium catalyst: (a). However, the unsatisfactory yield in the preparation of the aforementioned methacrylate led us to disregard this alternative. See, however: (b)
-
Attempts at preparing lactone 10 in a more direct way by RCM of the methacrylate of alcohol 7 with the standard ruthenium catalyst were unsuccessful (see Ref. 6). Very recently, a lactone with a conjugated trisubstituted C=C bond has been prepared by means of RCM with the aid of a second-generation ruthenium catalyst: (a) Cossy J., Bauer D., Bellosta V. Synlett. 2002;715-718. However, the unsatisfactory yield in the preparation of the aforementioned methacrylate led us to disregard this alternative. See, however: (b) Rodríguez S., Castillo E., Carda M., Marco J.A. Tetrahedron. 58:2002;1185-1192.
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(2002)
Tetrahedron
, vol.58
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Rodríguez, S.1
Castillo, E.2
Carda, M.3
Marco, J.A.4
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33
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33751386344
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(a) Wu W.-L., Wu Y.-L. J. Org. Chem. 58:1993;3586-3588 (b) Xie M., Berges D.A., Robins M.J. J. Org. Chem. 61:1996;5178-5179.
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Wu, W.-L.1
Wu, Y.-L.2
-
35
-
-
0012768220
-
-
note
-
4 were unsuccessful, however, and led only to reduction of the lactone carbonyl group.
-
-
-
-
37
-
-
0012875587
-
-
note
-
The reduction of the aldehyde function in the intermediate products resulting from oxidative cleavage of 10, ent-10 and 17 has to be performed at low temperature, otherwise reductive opening of the lactone ring becomes competitive.
-
-
-
-
38
-
-
0012769518
-
-
Part of the data presented here have been taken from the PhD Thesis of E. Castillo (Univ. Jaume I, Castellón, Spain, 2000)
-
Part of the data presented here have been taken from the PhD Thesis of E. Castillo (Univ. Jaume I, Castellón, Spain, 2000).
-
-
-
-
39
-
-
0012815295
-
-
Products of Michael addition to the conjugated double bond were detected during attempts at hydrolytic cleavage of the acetonide moiety in 15. In view of this, acetal hydrolysis was performed in saturated lactone 16 under carefully controlled conditions, as this compound was prone to translactonization and/or hydrolytic ring opening in acidic media
-
Products of Michael addition to the conjugated double bond were detected during attempts at hydrolytic cleavage of the acetonide moiety in 15. In view of this, acetal hydrolysis was performed in saturated lactone 16 under carefully controlled conditions, as this compound was prone to translactonization and/or hydrolytic ring opening in acidic media.
-
-
-
-
40
-
-
0012827099
-
-
Stronger Lewis acids caused destruction of the acetonide moiety (see Refs. 7 and 9)
-
Stronger Lewis acids caused destruction of the acetonide moiety (see Refs. 7 and 9).
-
-
-
-
42
-
-
0036329749
-
-
For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
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, pp. 2649-2655
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Carda, M.1
González, F.2
Castillo, E.3
Rodríguez, S.4
Marco, J.A.5
Eur6
-
43
-
-
0037031711
-
-
For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
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J. Org. Chem.
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Carda, M.1
Rodríguez, S.2
Segovia, B.3
Marco, J.A.4
-
44
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0037015429
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-
For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
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Falomir, E.2
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Carda, M.4
Marco, J.A.5
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45
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For recent contributions of our group, see: (a)
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For recent contributions of our group, see: (a) Carda M., González F., Castillo E., Rodríguez S., Marco J.A., Eur. J. Org. Chem. 2002;2649-2655 (b) Carda M., Rodríguez S., Segovia B., Marco J.A. J. Org. Chem. 67:2002;6560-6563 (c) Murga J., Falomir E., García-Fortanet J., Carda M., Marco J.A. Org. Lett. 2002;3447-3449 (d) Falomir E., Murga J., Carda M., Marco J.A. Tetrahedron Lett. 44:2003;539-541.
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Tetrahedron Lett.
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Falomir, E.1
Murga, J.2
Carda, M.3
Marco, J.A.4
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Colombo, C.3
Gennari, C.4
Scolastico, C.5
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