Two efficient methods of the conversion of camptothecin to mappicine ketone, an antiviral lead compound

Tetrahedron Letters

Volumn 39, Issue 5-6, 1998, Pages 431-432

  Das, Biswanath ^a   Madhusudhan, P ^a   Kashinatham, A ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CAMPTOTHECIN; MAPPICINE KETONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DEGRADATION; DRUG SYNTHESIS; MICROWAVE IRRADIATION; REACTION ANALYSIS;

EID: 0032576798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10539-1     Document Type: Article

References (14)

1. 1. Part II in the series "Synthetic Studies on Natural Products"; for Part I see, Das, B. and Srinivas, K.V.N.S. Indian J. Chem. 1995, 34B, 261. IICT Communication No. 3907.
2. 2. Wall, M.E., Wani, M.C.; Cook, C.E.; Palmer, K.H.; McPhail, A.T.; Sim, G.A. J. Am. Chem. Soc. 1966, 88, 3888.
3. 3. Gallo, R.C.; Whang-peng, J.; Adamson, R.H. J. Natl. Cancer Inst. 1971,46, 789.
4. 4. Wall, M.E.; Wani, M.C. Ann. Rev. Pharmacol. Toxicol. 1977, 17, 117.
5. 5. a) Pendrak, I.; Wittrock, R.; Kingsbury, W.D. J. Org. Chem. 1995, 60, 2912.
6. b) Pendrak, I.; Berney, S.; Wittrock, R.; Lambert, D, M.; Kingsbury, W.D. J. Org. Chem. 1994, 59, 2623.
7. 6. Kingsbury, W.D. Tetrahedron Lett. 1988, 29, 6847.
8. 7. a) Fortunak, J.M.D.; Mastrocola, A.R.; Mellinger, M.; Wood, J.L. Tetrahedron Lett. 1994, 35, 3763.;
9. b) Josien, H.; Curran, P. Tetrahedron, 1997, 53, 8881.
10. 8. a) Wu, T.-S.; Chan, Y.-Y.; Leu, Y.-L.; Chern, C.-Y.; Chen, C.-F. Phytochemistry, 1996, 42, 907.
11. b) Das, B.; Rao, S.P.; Kashinatham, A.; Srinivas, K.V.N.S. Indian J. Chem. 1997, 36B, 208.
12. c) During large-scale isolation of camptothecin from the stems of Indian Nothapodytes foetida we have isolated mappicine ketone (yield 0.0001%) and 9-methoxymappicine ketone (yield 0.0001%).
13. 3 to afford mappicine ketone (114mg). Unreacted camptothecin (54mg) was recovered.
14. 3 to yield mappicine ketone (168 mg).