Transformations of lignans. Part 11: Oxidation of diphyllin with hypervalent iodine reagents and reductive reactions of a resulting 1-methoxy-1-aryl-4-oxonaphthalene lactone

Tetrahedron

Volumn 62, Issue 18, 2006, Pages 4463-4473

  Venkateswarlu, R ^a   Kamakshi, C ^a   Subhash, P V ^a   Moinuddin, S G A ^a   Rama Sekhara Reddy, D ^a   Ward, R S ^b   Pelter, A ^b   Gelbrich, T ^c   Hursthouse, M B ^c   Coles, S J ^c   Light, M E ^c  

^a ANDHRA UNIVERSITY   (India)

^b SWANSEA UNIVERSITY   (United Kingdom)

^c UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

3,4 Dihydrodiphyllin; Benzyloxyoxime; Diphyllin; Lignans; Oxazinone; Oxidative nucleophilic substitutions; Synthesis

Indexed keywords

ALUMINUM; AMINE; BENZYLOXYAMINE; DIPROPHYLLINE; GAMMA LACTONE DERIVATIVE; HYDROXYLAMINE; IODINE; LACTONE DERIVATIVE; LIGNAN; LITHIUM; NAPHTHALENE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL;

EID: 33646098948     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.050     Document Type: Article

References (23)

1. Ward R.S. Phytochem Rev. 2 (2003) 391
2. Ward R.S. Synthesis (1992) 719
3. Ayres D.C., and Loike J.D. Lignans: Chemical, Biological and Clinical Properties (1990), Cambridge University Press, Cambridge
4. Charlton J.L. J. Nat. Prod. 61 (1998) 1447
5. Rodrigo R. Tetrahedron (1998) 2093
6. Ramachandra Row L., Venkateswarlu R., Pelter A., and Ward R.S. Tetrahedron Lett. 21 (1980) 2919
7. Pelter A., Ward R.S., Venkateswarlu R., and Kamakshi C. Tetrahedron 45 (1989) 3451
8. Pelter A., Ward R.S., Venkateswarlu R., and Kamakshi C. Tetrahedron 47 (1991) 1275
9. Pelter A., Ward R.S., Venkateswarlu R., and Kamakshi C. Tetrahedron 48 (1992) 7209
10. Anjaneyulu A.S.R., Santhikumar D., Venkateswarlu R., and Kamakshi C. Indian J. Chem., Sect. B 34 (1995) 897
11. Ward R.S., Pelter A., Venkateswarlu R., Kamakshi C., and Lakshmi A. Tetrahedron 52 (1996) 14349
12. Ward R.S., Pelter A., Venkateswarlu R., Kamakshi C., Subhash P.V., Moinuddin S.G.A., Hursthouse M.B., Coles S.J., and Hibbs D.E. Tetrahedron 55 (1999) 13071
13. Venkateswarlu R., Kamakshi C., Moinuddin S.G.A., Subhash P.V., Ward R.S., Pelter A., Hursthouse M.B., and Light M.E. Tetrahedron 55 (1999) 13087
14. Venkateswarlu R., Kamakshi C., Moinuddin S.G.A., Subhash P.V., Ward R.S., Pelter A., Hursthouse M.B., Light M.E., and Coles S.J. Tetrahedron 57 (2001) 5625
15. Pelter A., Ward R.S., and El-Ghani A. J. Chem. Soc., Perkin Trans. 1 (1996) 1353
16. Pelter A., Hussain A., Smith G., and Ward R.S. Tetrahedron 53 (1997) 5879
17. Pelter A., and Ward R.S. Tetrahedron 57 (2001) 273
18. Kürti L., Herczegh P., Visy J., Simonyi M., Antus S., and Pelter A. J. Chem. Soc., Perkin Trans. 1 (1999) 379
19. Pelter A., Satchwell P., Ward R.S., and Blake K. J. Chem. Soc., Perkin Trans. 1 (1995) 2201
20. Ward R.S., Pelter A., and Abd- El-Ghani A. Tetrahedron 52 (1996) 1303
21. Anjaneyulu A.S.R., Ramaiah P.A., Row L.R., Venkateswarlu R., Pelter A., and Ward R.S. Tetrahedron 37 (1981) 3641
22. Kunroda T., Takahashi M., Kondo K., and Iwasaki T. J. Org. Chem. 61 (1996) 9560
23. Jose M., del Corral M., Gordaliza M., Castro M.A., Vazquez M.L.L., Gracia-Gravalos M.D., Broughton H.B., and San Feliciano A. Tetrahedron 53 (1997) 6555