Discodermolide/Dictyostatin Hybrids: Synthesis and Biological Evaluation

Organic Letters

Volumn 4, Issue 25, 2002, Pages 4443-4446

  Shin, Youseung ^a   Choy, Nakyen ^a   Balachandran, Raghavan ^a   Madiraju, Charitha ^a   Day, Billy W ^a   Curran, Dennis P ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; ANTINEOPLASTIC AGENT; CARBAMIC ACID DERIVATIVE; DICTYOSTATIN; DISCODERMOLIDE; LACTONE; MACROLIDE; PYRONE DERIVATIVE;

ARTICLE; BREAST TUMOR; CELL CULTURE; CHEMISTRY; FEMALE; HUMAN; OVARY TUMOR; PATHOLOGY; SYNTHESIS;

ALKANES; ANTINEOPLASTIC AGENTS; BREAST NEOPLASMS; CARBAMATES; FEMALE; HUMANS; LACTONES; MACROLIDES; OVARIAN NEOPLASMS; PYRONES; TUMOR CELLS, CULTURED;

EID: 0037069732     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026942l     Document Type: Article

References (21)

1. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.; Schulte, G. K. J. Org. Chem. 1990, 55, 4912; (correction) 1991, 56, 1346.
2. (a) Ter Haar, E.; Kowalski, R. J.; Hamel, E.; Lin, C. M.; Longley, R. E.; Gunasekera, S. P.; Rosenkranz, H. S.; Day, B. W. Biochemistry 1996, 35, 243.
3. (b) Kowalski, R. J.; Giannakakou, P.; Gunasekera, S. P.; Longley, R. E.; Day, B. W.; Hamel, E. Mol. Pharmacol. 1997, 52, 613.
4. Paterson, I.; Florence, G. I.; Gerlach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535 and references therein.
5. (a) Hung, D. T.; Nerenberg, J. B.; Schreiber, S. L. J. Am. Chem. Soc. 1996, 118, 11054.
6. (b) Martello, L. A.; LaMarche, M. J.; He, L.; Beauchamp, T. J.; Smith, A. B., III; Horwitz, S. B. Chem. Biol. 2001, 8, 843.
7. (c) Isbrucker, R. A.; Gunasekera, S. P.; Longley, R. E. Cancer Chemother. Pharmacol. 2001, 48, 29.
8. (a) Pettit, G. R.; Linchacz, Z. A.; Gao, F.; Boyd, M. R.; Schmidt, J. M. J. Chem. Soc., Chem. Commun. 1994, 1111.
9. (b) The stereostructure is taken from the following patent: Pettit, G. R.; Cichacz, Z. A. US5430053, 1995. Given its similarity to discodermolide, dictyostatin-1 may be the enantiomer of 2.
10. For conformational studies of discodermolide, see: (a) Smith, A. B., III; LaMarche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695. (b) Monteagodo, E.; Cicero, D. O.; Cornett, B.; Myles, D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 123, 6929.
11. For conformational studies of discodermolide, see: (a) Smith, A. B., III; LaMarche, M. J.; Falcone-Hindley, M. Org. Lett. 2001, 3, 695. (b) Monteagodo, E.; Cicero, D. O.; Cornett, B.; Myles, D. C.; Snyder, J. P. J. Am. Chem. Soc. 2001, 123, 6929.
12. Furukawa, T.; Curran, D. P. Org. Lett. 2002, 13, 2233.
13. Heathcock, C. H.; Pirrung, M. C.; Montgomery, S. H.; Lampe, J. Tetrahedron 1981, 37, 4087.
14. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511.
15. (a) Andringa, H.; Heus Kloos, Y. A.; Brandsma, L. J. Organomet. Chem. 1987, 336, C41.
16. (b) Paterson, I.; Schlapbach, A. Synlett. 1995, 498.
17. Inanaga, J.; Kuniko, H.; Hiroko, S.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
18. Wipf, P.; Reeves, J. T.; Balachandran, R.; Giuliano, K. A.; Hamel, E.; Day, B. W. J. Am. Chem. Soc. 2000, 122, 9391.
19. Johansson, R.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1984, 2371.
20. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
21. Hamel, E.; Sacken, D. L.; Vourloumis, D.; Nicolaou, K. C. Biochemistry 1999, 38, 5490.