A simple construction of chiral fused benzoxocine ring ethers from D-glucose by regioselective 8-endo-aryl radical cyclisation

Chemical Communications

Volumn , Issue 22, 1997, Pages 2139-2140

  Chattopadhyay, Partha ^a   Mukherjee, Monika ^b   Ghosh, Soma ^b  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542474009     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706249d     Document Type: Article

References (23)

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2. Y.-Y. Lin, M. Risk, S. M. Roy, D. van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773; M. Murata, M. Kumagai, J. S. Lee and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto and H. Hirota, J. Am. Chem. Soc., 1992, 114, 1102; M. Satake, M. Murata and T. Yasumoto, Tetrahedron Lett., 1993, 34, 1975; M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361; M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 2060; T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
3. Y.-Y. Lin, M. Risk, S. M. Roy, D. van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773; M. Murata, M. Kumagai, J. S. Lee and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto and H. Hirota, J. Am. Chem. Soc., 1992, 114, 1102; M. Satake, M. Murata and T. Yasumoto, Tetrahedron Lett., 1993, 34, 1975; M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361; M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 2060; T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
4. Y.-Y. Lin, M. Risk, S. M. Roy, D. van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773; M. Murata, M. Kumagai, J. S. Lee and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto and H. Hirota, J. Am. Chem. Soc., 1992, 114, 1102; M. Satake, M. Murata and T. Yasumoto, Tetrahedron Lett., 1993, 34, 1975; M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361; M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 2060; T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
5. Y.-Y. Lin, M. Risk, S. M. Roy, D. van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773; M. Murata, M. Kumagai, J. S. Lee and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto and H. Hirota, J. Am. Chem. Soc., 1992, 114, 1102; M. Satake, M. Murata and T. Yasumoto, Tetrahedron Lett., 1993, 34, 1975; M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361; M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 2060; T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
6. Y.-Y. Lin, M. Risk, S. M. Roy, D. van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773; M. Murata, M. Kumagai, J. S. Lee and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto and H. Hirota, J. Am. Chem. Soc., 1992, 114, 1102; M. Satake, M. Murata and T. Yasumoto, Tetrahedron Lett., 1993, 34, 1975; M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361; M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 2060; T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
7. Y.-Y. Lin, M. Risk, S. M. Roy, D. van Engen, J. Clardy, J. Golik, J. C. James and K. Nakanishi, J. Am. Chem. Soc., 1981, 103, 6773; M. Murata, M. Kumagai, J. S. Lee and T. Yasumoto, Tetrahedron Lett., 1987, 28, 5869; H. Nagai, K. Torigoe, M. Satake, M. Murata, T. Yasumoto and H. Hirota, J. Am. Chem. Soc., 1992, 114, 1102; M. Satake, M. Murata and T. Yasumoto, Tetrahedron Lett., 1993, 34, 1975; M. Satake, M. Murata and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 361; M. Murata, H. Naoki, T. Iwashita, S. Matsunaga, M. Sasaki, A. Yokoyama and T. Yasumoto, J. Am. Chem. Soc., 1993, 115, 2060; T. Yasumoto and M. Murata, Chem. Rev., 1993, 93, 1897.
8. For the synthesis of 8-membered condensed ether ring systems, see J.-i. Yamada, T. Asano, I. Katoda and Y. Yamamoto, J. Org. Chem., 1990, 55, 6066; E. Alvarez, M.-L. Candenas, R. Perez, J. L. Ravelo and J. D. Martin, Chem. Rev., 1995, 95, 1953; K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589 and references cited therein; E. Alvarez, M. Delgado, M. T. Diaz, L. Hanxing, R. Perez and J. D. Martin, Tetrahedron Lett., 1996, 37, 2865; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 and 127.
9. For the synthesis of 8-membered condensed ether ring systems, see J.-i. Yamada, T. Asano, I. Katoda and Y. Yamamoto, J. Org. Chem., 1990, 55, 6066; E. Alvarez, M.-L. Candenas, R. Perez, J. L. Ravelo and J. D. Martin, Chem. Rev., 1995, 95, 1953; K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589 and references cited therein; E. Alvarez, M. Delgado, M. T. Diaz, L. Hanxing, R. Perez and J. D. Martin, Tetrahedron Lett., 1996, 37, 2865; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 and 127.
10. For the synthesis of 8-membered condensed ether ring systems, see J.-i. Yamada, T. Asano, I. Katoda and Y. Yamamoto, J. Org. Chem., 1990, 55, 6066; E. Alvarez, M.-L. Candenas, R. Perez, J. L. Ravelo and J. D. Martin, Chem. Rev., 1995, 95, 1953; K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589 and references cited therein; E. Alvarez, M. Delgado, M. T. Diaz, L. Hanxing, R. Perez and J. D. Martin, Tetrahedron Lett., 1996, 37, 2865; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 and 127.
11. For the synthesis of 8-membered condensed ether ring systems, see J.-i. Yamada, T. Asano, I. Katoda and Y. Yamamoto, J. Org. Chem., 1990, 55, 6066; E. Alvarez, M.-L. Candenas, R. Perez, J. L. Ravelo and J. D. Martin, Chem. Rev., 1995, 95, 1953; K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589 and references cited therein; E. Alvarez, M. Delgado, M. T. Diaz, L. Hanxing, R. Perez and J. D. Martin, Tetrahedron Lett., 1996, 37, 2865; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 and 127.
12. For the synthesis of 8-membered condensed ether ring systems, see J.-i. Yamada, T. Asano, I. Katoda and Y. Yamamoto, J. Org. Chem., 1990, 55, 6066; E. Alvarez, M.-L. Candenas, R. Perez, J. L. Ravelo and J. D. Martin, Chem. Rev., 1995, 95, 1953; K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1996, 35, 589 and references cited therein; E. Alvarez, M. Delgado, M. T. Diaz, L. Hanxing, R. Perez and J. D. Martin, Tetrahedron Lett., 1996, 37, 2865; J. S. Clark and J. G. Kettle, Tetrahedron Lett., 1997, 38, 123 and 127.
13. For the synthesis of 9-membered ether ring systems, see M. Inoue, M. Sasaki and K. Tachibana, Tetrahedron Lett., 1997, 38, 1611 and references cited therein.
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