First straightforward synthesis of 1-hydroxy-3,4-dihydro-1H-benz[g]isochromene-5,10-dione and structure revision of a bioactive benz[g]isochromene-5,10-dione from Psychotria camponutans

Tetrahedron

Volumn 64, Issue 2, 2008, Pages 412-418

  Jacobs, Jan ^a   Claessens, Sven ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Plasmodium falciparum; Psychorubrin; Psychotria camponutans; Psychotria rubra; Pyranonaphthoquinones; Quinones

Indexed keywords

1 HYDROXY 3,4 DIHYDRO 1H BENZ[G]ISOCHROMENE 5,10 DIONE; 3 CYANO 1(3H) ISOBENZOFURANONE; 5,6 DIHYDROPYRAN 2 ONE; CHROMENE DERIVATIVE; FURANONE DERIVATIVE; LACTONE; PHTHALIDE DERIVATIVE; PYRAN DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PSYCHOTRIA; SYNTHESIS;

PLASMODIUM FALCIPARUM; PSYCHOTRIA CAMPONUTANS; PSYCHOTRIA RUBRA;

EID: 36448949039     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.063     Document Type: Article

References (21)

1. Hari L., De Buyck L.F., and De Pooter H.L. Phytochemistry 30 (1991) 1726-1727
2. De Kimpe N., Van Puyvelde L., Schripsema J., Erkelens C., and Verpoorte R. Magn. Reson. Chem. 31 (1993) 329-330
3. Van Puyvelde, L.; Hakizayezu, D.; Brioen, P.; De Kimpe, N.; De Vroey, C.; Bogaerts, J.; Hakizamungu, E. International Research Congress on Natural Products, Halifax, Nova Scotia, Canada, July 31-August 4, 1994; p 119.
4. For a recent review on the isolation and the synthesis of pentalongin and related pyranonaphtoquinones, see:. Claessens S., Verniest G., Jacobs J., Van Hende E., Habonimana P., Nguyen Van T., Van Puyvelde L., and De Kimpe N. Synlett (2007) 829-850
5. Hayashi T., Smith F.T., and Lee K.-H. J. Med. Chem. 30 (1987) 2005-2008
6. Solis P.N., Lang'at C., Gupta M.P., Kirby G.C., Warhurst D.C., and Phillipson J.D. Planta Med. 61 (1995) 62-65
7. Phillipson J.D. Phytochemistry 38 (1995) 1319-1343
8. Hauser F.M., and Rhee R.P. J. Org. Chem. 43 (1978) 178-180
9. Kraus G.A., and Sugimoto H. Tetrahedron Lett. 19 (1978) 2263-2266
10. Kraus G.A., Cho H., Crowley S., Roth B., Sugimoto H., and Prugh S. J. Org. Chem. 48 (1983) 3439-3444
11. Pahari P., Senapati P., and Mal D. Tetrahedron Lett. 48 (2007) 2635-2638 For reviews on the use of the phthalide annulation reaction in organic synthesis:
12. Mitchell A.S., and Russell R.A. Tetrahedron 51 (1995) 5207-5236
13. Rathwell K., and Brimble M.A. Synthesis (2007) 643-662
14. Freskos J.N., Morrow G.W., and Swenton J.S. J. Org. Chem. 50 (1985) 805-810
15. Examples can be found in:
16. Jacobs J., Claessens S., Kesteleyn B., Huygen K., and De Kimpe N. Tetrahedron 63 (2007) 2503-2510
17. Claessens S., Verniest G., El Hady S., Nguyen Van T., Kesteleyn B., Van Puyvelde L., and De Kimpe N. Tetrahedron 62 (2006) 5152-5158
18. Claessens S., Naidoo D., Mulholland D., Verschaeve L., van Staden J., and De Kimpe N. Synlett (2006) 621-623
19. Kesteleyn B., De Kimpe N., and Van Puyvelde L. J. Org. Chem. 64 (1999) 1173-1179
20. Kesteleyn B., De Kimpe N., and Van Puyvelde L. Synthesis (1999) 1881-1883
21. Nguyen Van T., and De Kimpe N. Tetrahedron Lett. 45 (2004) 3443-3446