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19
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0000927780
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We are also investigating a different approach to the total synthesis of 1 based on an intramolecular [4+2] cycloaddition: see a) Y. Kita, R. Okunaka, T. Honda, M. Shindo, O. Tamura, Tetrahedron Lett. 1989, 30, 3995-3998;
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A similar intramolecular strategy was reported separately: see e) M. Toyota, S. Terashima, Terahedron Lett. 1989, 30, 829-832.
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24
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2742578380
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For a study on construction of optically active quaternary carbon in connection with 1: see W. Trypke, A. Steigel, M. Braun, Synlett 1992, 827-829.
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28
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85004434450
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Application of this method to the total syntheses of peri-hydroxy polyaromatic compounds: see reviews, a) Y. Tamura, Y. Kita, Yuki Gosei Kagaku Kyokaishi 1988, 46, 205-217
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See also other examples done by other groups, d) F. Matsuda, M. Kawasaki, M. Ohsaki, K. Yamada, S. Terashima, Tetrahedron 1988, 44, 5745-5759;
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e) J.-F. Lavallée, R. Rej, M. Courchesne, D. Nguyen, G. Attardo, Tetrahedron Lett. 1993, 34, 3519-3522;
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g) M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou, S. J. Danishefsky, J. Am. Chem. Soc. 1996, 118, 9509-9525.
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Y. Kita, S. Kitagaki, R. Imai, S. Okamoto, S. Mihara, Y. Yoshida, S. Akai, H. Fujioka, Tetrahedron Lett. 1996, 37, 1817-1820.
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8544276578
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See also, Y. Kita, S. Kitagaki, Y. Yoshida, S. Mihara, D.-F. Fang, M. Kondo, S. Okamoto, R. Imai, S. Akai, H. Fujioka, J. Org. Chem. 1997, 62, 4991 - 4997;
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40
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33747531180
-
-
note
-
The enone 3 was obtained from methyl 2-methoxy-4,6-dimethylpyridine-3-carboxylate as per Scheme 5. The details will be presented in the forthcoming full paper. (Chemical Equation Presented) Scheme 5. Synthesis of 3.
-
-
-
-
41
-
-
33845282438
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-
E. J. Corey, R. K. Bakshi, S. Shibata, C.-P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925-7926.
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Singh, V.K.5
-
42
-
-
33747550049
-
-
note
-
Optical purities of the intermediates (5, 6, and 9) were determined by HPLC using Daicel CHIRALCEL OD (n-hexane-iPrOH), and those of 2, 7, 8, (R)- and (S)-14, and (S)-15 by Daicel CHIRALPAK AD (n-hexane-iPrOH).
-
-
-
-
43
-
-
33747531839
-
-
note
-
Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-102892 (for (-)-2), CCDC-102893 (for (+)-7), and CCDC-102894 {for methyl 2-methoxy-2-[3,4,6-trimethoxy-2-(methoxycarbonyl)phenyl]acetate, a precursor of 13}. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
-
-
-
-
44
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33747574646
-
-
note
-
[11c]
-
-
-
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46
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0000221441
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Y. Kita, S. Akai, N. Ajimura, M. Yoshigi, T. Tsugoshi, H. Yasuda, Y. Tamura, J. Org. Chem. 1986, 51, 4150-4158.
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47
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0028265202
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Y. Kita, H. Ueno, S. Kitagaki, K. Kobayashi, K. Iio, S. Akai, J. Chem. Soc. Chem. Commun. 1994, 701-702.
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Iio, K.5
Akai, S.6
-
48
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-
33747535905
-
-
note
-
3COOH.
-
-
-
|