6) Acknowledgments and References


We are grateful to Dr. M. G. B. Zoghbi for providing us the spectral data of the authentic sample of oxo-parabenzlactone and the Ministry of Education, Science, Sports, and Culture of Japan and the Science Research Promotion Fund of the Japan Private School Promotion Foundation for research grants.


  1. Neilson, D. G. The Chemistry of Amidines and Imidates; vol. 2, Patai, S.; Rappoport, Z. eds.; John Wiley and Sons, Inc.: Chichester, 1991; pp. 425-483. [back to the Part 1)]

  2. 3, 3-Sigmatropic rearrangement of hydroximate has been previously reported as a method for synthesis of N-allylhydroxamic acid. De La Torre, J. A.; Fernandez, M.; Morgans, D.; Smith, Jr. D. B.; Talamas, F. X.; Trejo, A. Tetrahedron Lett. 1994, 35, 15-18. [back to the Part 1)]

  3. We have reported thiyl radical addition-cyclization of dienylamides for lactam synthesis. (a) Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc. Perkin Trans. 1. 1995, 19-26; (b) Naito, T.; Honda, Y.; Miyata, O.; Ninomiya, I. Chem. Pharm. Bull. 1993, 41, 217-219. [back to the Part 1)]

  4. Lactone syntheses by radical cyclization: (a) Walling, C.; Cooley, J. H.; Ponaras, A. A.; Racah, E. J. J. Am. Chem. Soc. 1966, 88, 5361-5363; (b) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566; (c) Stork, G.; Mook, R.; Biller, Jr. S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741-3742; (d) Belletire, J. L.; Mohmoodi, N. O. Tetrahedron Lett. 1989, 30, 4363-4366; (e) Hanessian, S.; Fabio, R. D.; Marcoux, J.-F.; Prud'homme, M. J. Org. Chem. 1990, 55, 3436-3438; (f) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750; (g) Fukuzawa, S.; Tsuchimoto, T. Synlett 1993, 803-804. [back to the Part 1)]

  5. The substrates 4a-d, 7, 10a-d, and 16 were prepared according to the reported procedure; Johnson, J. E.; Springfield, J. R.; Hwang, J. S.; Hayes, L. J.; Cunningham, W. C.; McClaugherty, D. L. J. Org. Chem. 1971, 36, 284-294. [back to the Part 2)] [back to the Part 4)]

  6. Structures of the stereoisomeric hydroximates 5a-d and 6a-d were established by irreversible isomerization of cis-hydroximates 5a-d to trans-isomers 6a-d with sodium ethoxide and single-crystal X-ray analysis of cis-5a. Stereostructures of the cyclic hydroximates 11a-d and 12a-d were established by their NMR spectra including NOESY spectra. Crystal data of cis-5a: C19H21NO2S, space group Pbca with a=18.131 (3), b= 26.611 (2), c= 14.575 (1) Å, V= 7032.4 (1.5) Å3. Final R value was 0.060 for 5980 reflections. [back to the Part 2)]

  7. This reaction condition has been developed