A facile route to 3,7-cis-disubstituted cycloocta-1,5-diene-1,2,5,6-tetracarboxylates through photochemical [2 + 2]cycloaddition of 3-substituted cyclobutene-1,2-dicarboxylates and thermal isomerization

Chemical Communications

Volumn , Issue 17, 1999, Pages 1753-1754

  Watanabe, Hisayuki ^a   Nakajima, Yasuyuki ^a   Adachi, Michiaki ^a   Hotta, Hiroyasu ^a   Arai, Kazutaka ^a   Baba, Yoshiyasu ^b   Noutary, Carole ^b   Ichikawa, Satsuki ^b   Kusumoto, Tetsuo ^b   Hiyama, Tamejiro ^c  

^a NISSAN CHEMICAL INDUSTRIES LTD   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DIMERIZATION; ISOMERISM; PHOTOCHEMISTRY; STEREOCHEMISTRY;

EID: 0033533518     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903942b     Document Type: Article

References (13)

1. T. Watanabe, K. Yasumoto, M. Murata, M. Tagawa, H. Narushima, T. Furusato, M. Kuwahara, M. Hanaue and T. Seki, Jpn. Kokai Tokkyo Koho, 1994, JP 06-184157, EP 582267, US 5346919; Chem. Abstr., 1994, 121, 7432t.
2. T. Watanabe, K. Yasumoto, M. Murata, M. Tagawa, H. Narushima, T. Furusato, M. Kuwahara, M. Hanaue and T. Seki, Jpn. Kokai Tokkyo Koho, 1994, JP 06-184157, EP 582267, US 5346919; Chem. Abstr., 1994, 121, 7432t.
3. N. A. Petasis and M. A. Patane, Tetrahedron, 1992, 48, 5757.
4. Y. Baba, C. Noutary, S. Ichikawa, T. Kusumoto, H. Watanabe, M. Adachi, H. Hotta, Y. Nakajima, K. Arai and T. Hiyama, Synlett, 1997, 1393.
5. Houben Weyl, 4/5a, 344-345, 352, 500-501; E. Vogel, O. Roos and K.-H. Disch, Justus Liebigs Ann. Chem., 1962, 653, 55; D. Bellus, K. Bredow, H. Sauter and G. D. Weis, Helv. Chim. Acta, 1973, 56, 3004; K. I. Booker-Milburn, F. D. Jimenez and A. Sharpe, Synlett, 1995, 735.
6. Houben Weyl, 4/5a, 344-345, 352, 500-501; E. Vogel, O. Roos and K.-H. Disch, Justus Liebigs Ann. Chem., 1962, 653, 55; D. Bellus, K. Bredow, H. Sauter and G. D. Weis, Helv. Chim. Acta, 1973, 56, 3004; K. I. Booker-Milburn, F. D. Jimenez and A. Sharpe, Synlett, 1995, 735.
7. Houben Weyl, 4/5a, 344-345, 352, 500-501; E. Vogel, O. Roos and K.-H. Disch, Justus Liebigs Ann. Chem., 1962, 653, 55; D. Bellus, K. Bredow, H. Sauter and G. D. Weis, Helv. Chim. Acta, 1973, 56, 3004; K. I. Booker-Milburn, F. D. Jimenez and A. Sharpe, Synlett, 1995, 735.
8. Houben Weyl, 4/5a, 344-345, 352, 500-501; E. Vogel, O. Roos and K.-H. Disch, Justus Liebigs Ann. Chem., 1962, 653, 55; D. Bellus, K. Bredow, H. Sauter and G. D. Weis, Helv. Chim. Acta, 1973, 56, 3004; K. I. Booker-Milburn, F. D. Jimenez and A. Sharpe, Synlett, 1995, 735.
9. J. D. White, M. P. Dillon and R. J. Butlin, J. Am. Chem. Soc., 1992, 114, 9673.
10. Products 3d and 3e formed as inseparable mixtures of isomers due to asymmetric carbons of side chains.
11. ++1), 453, 425, 411.
12. 3) 0.98 (t, J 7.2, 6H), 1.41-1.50 (m, 4H), 1.58-1.67 (m, 2H), 1.74-1.83 (m, 2H), 2.91-3.05 (m, 6H).
13. M. Adachi, Y. Nakajima, H. Watanabe, H. Hotta, K. Arai, M. Tagawa, M. Futagawa, T. Furusato, H. Ohya, Y. Baba, C. Noutary, S. Ichikawa, T. Kusumoto and T. Hiyama, 'The 21st IUPAC International Symposium on The Chemistry of Natural Products,' Chinese Chem. Soc., Beijing, 1998, p. 169. Zopfiellin and its analogs 1a and 1c exhibit fungicidal activity at 100 ppm (in vitro) against Botorytis cinerea. Detailed results of the assay will be reported elsewhere.