Synthesis of Naturally Occurring (Z)-3-Benzylidenephthalide and (±) 3-Benzylphthalides

(Note: The full text of this document is currently only available in the PDF Version )

Raghao S. Mali, Archna P. Massey and Manohar I. Talele


Abstract

A convenient method, involving the generation of the phthalide anion, is described for the synthesis of naturally occurring (Z)-3-benzylidenephthalide (5) and (±) 3-benzylphthalides (6c, 10ac), starting from phthalides (7a and 7b).


References

  1. (a) R. A. Aitken, H. R. Cooper and A. P. Mehrotra, J. Chem. Soc., Perkin Trans. 1, 1996, 475 RSC ; (b) Y. Masahisa, K. Kenshi, K. Takaki, A. Michitaka, K. Toshio and O. Nobuhiro, J. Med. Chem., 1993, 36, 4052 CrossRef ; (c) T. Nishio, J. Chem. Soc., Perkin Trans. 1, 1995, 561 RSC ; (d) E. Napolitano, R. Fiaschi, V. Scartoni and A. Marsili, J. Chem. Soc., Perkin, Trans. 1, 1986, 781 RSC .
  2. M. Yoshikawa, E. Uchida, N. Chatani, N. Murakami and J. Yamahara, Chem. Pharm. Bull., 1992, 40, 3121 CAS .
  3. L. Kraut, R. Mues and M. Sim Sim, Phytochemistry, 1994, 37, 1337 CrossRef CAS .
  4. Y. Asakawa, K. Takikawa, M. Tori and E. O. Campbell, Phytochemistry, 1986, 25, 2543 CrossRef CAS .
  5. (a) Y. Asakawa, K. Takikawa and M. Tori, Phytochemistry, 1987, 26, 1023 CrossRef CAS ; (b) personal communication from Professor Asakawa .
  6. (a) M. Noda, M. Yamaguchi, E. Ando, K. Takeda and K. Nokihara, J. Org. Chem., 1994, 59, 7968 CrossRef CAS ; (b) B. S. Joshi, Q. Jiang, T. Rho and S. W. Pelletier, J. Org. Chem., 1994, 59, 8220 CrossRef CAS ; (c) T. A. Crabb and A. Patel, J. Chem. Soc., Perkin Trans. 1, 1982, 2783 RSC ; (d) N. E. Cundasawmy and D. B. MacLean, Can. J. Chem., 1972, 50, 3028 CAS ; (e) T. Takada and S. Ohki, Chem. Pharm. Bull., 1971, 19, 977 CAS .
  7. S. Ohta, Y. Kamata, T. Inagaki, Y. Masuda, S. Yamamoto, M. Yamashita and I. Kawasaki, Chem. Pharm. Bull., 1993, 41, 1188 CAS .
  8. M. Yoshikawa, E. Harada, N. Yagi, Y. Okuno, O. Muraoka, H. Aoyama and N. Murakami, Chem. Pharm. Bull., 1994, 42, 721 CAS .
  9. Zhi-Wei Wang, Shao-Bai Li and Yu-Lin Li, Indian J. Chem., 1996, 35B, 363 Search PubMed .
  10. M. I. Talele, M. Phil. Dissertation, University of Pune, 1986 .
  11. R. S. Mali, P. G. Jagtap, S. R. Patil and P. N. Pawar, J. Chem. Soc. Chem. Commun, 1992, 883 RSC .
  12. R. S. Mali, P. G. Jagtap and S. G. Tilve, Synth. Commun, 1990, 20, 2641 CAS .
  13. J. A. McRae, R. B. VanOrder, F. H. Griffiths and T. E. Habgood, Can. J. Chem., 1951, 29, 482 CAS .
Click here to see how this site uses Cookies. View our privacy policy here.