The first total synthesis of (±)-cyclophostin and (±)-cyclipostin P: Inhibitors of the serine hydrolases acetyl cholinesterase and hormone sensitive lipase

Organic Letters

Volumn 13, Issue 12, 2011, Pages 3094-3097

  Malla, Raj K ^a   Bandyopadhyay, Saibal ^a   Spilling, Christopher D ^a   Dutta, Supratik ^a   Dupureur, Cynthia M ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE INHIBITOR; CYCLIPOSTIN P; CYCLOPHOSTIN; ORGANOPHOSPHORUS COMPOUND; TRIACYLGLYCEROL LIPASE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HUMAN; IC 50; STEREOISOMERISM; SYNTHESIS;

CHOLINESTERASE INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; LIPASE; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM;

EID: 79958830175     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200991x     Document Type: Article

References (39)

1. Kurokawa, T.; Suzuki, K.; Hayaoka, T.; Nakagawa, T.; Izawa, T.; Kobayashi, M.; Harada, N. J. Antibiot. 1993, 46, 1315
2. - as P=O and hence assign the priority incorrectly. Natural cyclophostin is actually 3a R,6 R. See: Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. 1966, 5, 385. The configuration is correctly named in chemical abstracts
3. Wink, J.; Schmidt, F.-R.; Seibert, G.; Aretz, W. J. Antibiot. 2002, 55, 472
4. Věrtesy, L.; Beck, B.; Brönstrup, M.; Ehrlich, K.; Kurz, M.; Muller, G.; Schummer, D.; Seibert, G. J. Antibiot. 2002, 55, 480
5. Sakuda, S.; Tanaka, S.; Mizuno, K.; Sukcharoen, O.; Nihira, T.; Yamada, Y. J. Chem. Soc., Perkin Trans. 1 1993, 2309
6. Kato, J.; Funa, N.; Watanabe, H.; Ohnishi, Y.; Horinouchi, S. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 2378
7. Ohnishi, Y.; Kameyama, S.; Onaka, H.; Horinouchi, S. Mol. Microbiol. 1999, 34, 102
8. Miyake, K.; Horinouchi, S.; Yoshida, M.; Chiba, N.; Mori, K.; Nogawa, N.; Morikawa, N.; Beppu, T. J. Bacteriol. 1989, 171, 4298
9. Campbell, M. M.; Fox, J. L.; Sainsbury, M.; Liu, Y. Tetrahedron 1989, 45, 4551
10. Li, W. M.; Kan, K. K.; Carlier, P. R.; Pang, Y. P.; Han, Y. F. Curr. Alzheimer Res. 2007, 4, 386
11. Garcia-Carrasco, M.; Escárcega, R. O.; Fuentes-Alexandro, S.; Riebeling, C.; Cervera, R. Autoimmun. Rev. 2007, 6, 373
12. Kaur, J.; Zhang, M.-Q. Curr. Med. Chem. 2000, 3, 273
13. Holm, C.; Osterlund, T.; Laurell, H.; Conteras, J. A. Annu. Rev. Nutr. 2000, 20, 365
14. Yeaman, S. J. Biochem. J. 2004, 379, 11
15. Bandyopadhyay, S.; Dutta, S.; Spilling, C. D.; Dupureur, C. M.; Rath, N. P. J. Org. Chem. 2008, 73, 8386
16. For examples, see: Gadir, S. A.; Smith, Y.; Taha, A. A.; Thaller, V. J. Chem. Res (S) 1986, 222
17. Yoda, H.; Mizutani, M.; Takabe, K. Synlett 1998, 855
18. Sengoku, T.; Suzuki, T.; Kakimoto, T.; Takahashi, M.; Yoda, H. Tetrahedron 2009, 65, 2415
19. For examples, see: Banfi, L.; Basso, A.; Guanti, G.; Zannetti, M. T. Tetrahedron: Asymmetry 1997, 8, 4079
20. Parsons, P. J.; Lacrouts, P.; Buss, A. D. Chem. Commun. 1995, 437
21. Crawforth, J. M.; Fawcett, J.; J. Rawlings, B. J. Chem. Soc., Perkin Trans. 1 1998, 1721
22. Posner, G. H.; Wietzberg, M.; Jew, S.-S. Synth. Commun. 1987, 17, 611
23. Takabe, K.; Mase, N.; Matsumura, H.; Hasegawa, T.; Iida, Y.; Kuribayashi, H.; Adachi, K.; Yoda, H.; Ao, M. Bioorg. Med. Chem. Lett. 2002, 12, 2295
24. Mori, K.; Chiba, N. Liebigs Ann. Chem. 1989, 957
25. Takabe, K.; Tanaka, M.; Sugimoto, M.; Yamada, T.; Yoda, H. Tetrahedron: Asymmetry 1992, 3, 1385
26. For examples, see: Jacks, T. E.; Nibbe, H.; Wiemer, D. F. J. Org. Chem. 1993, 58, 4584
27. Singh, A. K.; Rao, M. N.; Simpson, J. H.; Li, W.-S.; Thornton, J. E.; Kuehner, D. E.; Kacsur, D. J. Org. Process Res. Dev. 2002, 6, 618
28. Krawczyk, H.; Wasek, K.; Kedzia, J.; Wojciechowski, J.; Wolf, W. M. Org. Biomol. Chem. 2008, 6, 308
29. The reaction of phosphates with NaI is generally performed in acetone, but other solvent including MeCN also work well. See: Zervas, L.; Dilaris, I. J. Am. Chem. Soc. 1955, 77, 5354
30. Smith, M.; Drummond, G. I.; Khorana, H. G. J. Am. Chem. Soc. 1961, 83, 698
31. Smith, M.; Moffatt, J. G.; Khorana, H. G. J. Am. Chem. Soc. 1958, 80, 6204
32. Khorana, H. G.; Tener, G. M.; Wright, R. S.; Moffatt, J. G. J. Am. Chem. Soc. 1957, 79, 430
33. The details of the structure determination have been deposited at the Cambridge Crystallographic Data Center as CCDC 812559.
34. Rai, A. N.; Basu, A. Tetrahedron Lett. 2003, 44, 2267
35. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139
36. Dutta, S.; Malla, R. K.; Bandyopadhyay, S.; Spilling, C. D.; Dupureur, C. M. Bioorg. Med. Chem. 2010, 18, 2265
37. White, J. D.; Kawasaki, M. J. Org. Chem. 1992, 57, 5292
38. Lichtenenthaler, F. W. Chem. Rev. 1961, 61, 607
39. Ellman, G. J.; Courtney, K. D., Jr.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88-95