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

Abstract

A regioselective 8-endo-trig aryl radical cyclisation of the 5,6-deoxy-D-xylo-5-enofuranosides 3a and 3b with tri-n-butyltin hydride provides the chiral furo[3,2-c][2]benzoxocines 4a and 4b in good yields; the crystal structure of 4a is reported.

References

1. 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.
2. 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.
3. 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.
4. A. Bhattacharjya, P. Chattopadhyay, A. T. McPhail and D. R. McPhail, J. Chem. Soc., Chem. Commun., 1990, 1508; 1991, 136; P. M. Collins, M. S. Ashwood, H. Eder, S. H. B. Wright and D. J. Kennedy, Tetrahedron Lett., 1990, 31, 2055; S. Dutta, P. Chattopadhyay, R. Mukhopadhyay and A. Bhattacharjya, Tetrahedron Lett., 1993, 34, 3585; T. K. M. Shing, W.-C. Fung and C.-H. Wong, J. Chem. Soc., Chem. Commun., 1994, 449; A. Bhattacharjee, A. Bhattacharjya and A. Patra, Tetrahedron Lett., 1995, 35, 4677.
5. A. V. R. L. Sudha and M. Nagarajan, J. Chem. Soc., Chem. Commun., 1996, 1359 and references cited therein.
6. K. Ghosh, A. K. Ghosh and U. R. Ghatak, J. Chem. Soc., Chem. Commun., 1994, 629.
7. P. J. Garegg and B. Samuelsson, Synthesis, 1979, 469.
8. G. Stork and N. H. Baine, J. Am. Chem. Soc., 1982, 104, 2321.