A high yield preparation of 2-fluoropodophyllotoxin

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2259-2262

  VanVliet, David S ^a   Lee, Kuo Hsiung ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUOROPODOPHYLLOTOXIN; ETOPOFOS; ETOPOSIDE; NATURAL PRODUCT; PODOPHYLLOTOXIN; TENIPOSIDE; TOXIN; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG MANUFACTURE; DRUG SYNTHESIS; FLUORINATION; NONHUMAN; PRODUCTIVITY; STEREOSPECIFICITY; TOXIN ANALYSIS;

EID: 0033583155     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00220-8     Document Type: Article

References (17)

1. 1. Antitumor Agents 193. For part 192 see Guan, J.; Zhu, X. K.; Brossi, A.; Tachibana, Y.; Bastow, K. F.; Verdier-Pinard, P.; Hamel, E.; McPhail, A. T.; Lee, K. H. Coll. Czech. Chem. Commun. in press.
2. 2. Tyring, S.; Edwards, L.; Cherry, L. K.; Ramsdell, W. M.; Kotner, S.; Greenberg, M. D.; Vance, J. C.; Barnum, G.; Dromgoole, S. H.; Killey, F. P.; Toter, T. Arch. Dermatology 1998, 134, 33-38.
3. 3. Belani, C. P.; Doyle, L. A.; Aisner, J. Cancer Chemo. Pharmac. 1994, 34 Suppl:S118-126.
4. 4. Witterland, A. H.; Koks, C. H.; Beijnen, J. H. Pharmacy World Sci. 1996, 18, 163-170.
5. 5. Choy, W. Genelabs Technologies, Inc., personal communication.
6. 6. Cragg, G.; Suffness, M. Pharmac. Ther. 1988, 37, 425.
7. 7. Gensler, W. J.; Gatsonis, C. D. J. Org. Chem. 1966, 31, 3224-3227.
8. 8. Gensler, W. J.; Murthy, C. D.; Trammell, M. H. J. Med. Chem. 1977, 20, 635-644.
9. 9. Glinski, M. B.; Freed, J. C.; Durst, T. J. Org. Chem. 1987, 52, 2749-2753.
10. 3),71.70 (C-11), 73.04 (C-4), 101.27 (C-14), 106.95 (C-5), 108.06 (C-2′), 109.36 (C-8), 131.10 (C-9), 133.65 (C-10), 135.35 (C-1′), 136.90 (C-4′), 147.35 (C-6), 147.36 (C-7), 152.49 (C-3′), 174.32 (C-13).
11. 11. Corey, E. J., Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190-6192.
12. 12. Davis, F. A.; Han, W.; Murphy, C. K.; J. Org. Chem. 1995, 60, 4730-4737.
13. 13. Differding, E.; Ofner, H., Synlett 1991, 187 and 395.
14. 14. For an excellent review on electrophilic fluorination see: Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737-1755.
15. 1/2F = 10.9 Hz).
16. 16. Davis, F. A.; Han, W. Tetrahedron Lett. 1992, 33, 1153-1156.
17. 1/2F = 12.1 Hz).