Absolute stereochemistries and total synthesis of (+)-arisugacins a and B, potent, orally bioactive and selective inhibitors of acetylcholinesterase

Tetrahedron

Volumn 60, Issue 36, 2004, Pages 7845-7859

  Sunazuka, Toshiaki ^a,b   Handa, Masaki ^a   Nagai, Kenichiro ^a   Shirahata, Tatsuya ^b   Harigaya, Yoshihiro ^a   Otoguro, Kazuhiko ^b   Kuwajima, Isao ^a   Omura, Satoshi ^a,b  

^a KITASATO UNIVERSITY   (Japan)

^b KITASATO INSTITUTE   (Japan)

Author keywords

Pyrone; 6 Electron electrocyclic ring closure; AChE inhibitor; Inversion of stereochemistry; Meroterpenoid; Stereoselective dihydroxylation

Indexed keywords

ALDEHYDE DERIVATIVE; ARISUGACIN A; ARISUGACIN B; CHOLINESTERASE INHIBITOR; PYRONE DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEOXYGENATION; DIHYDROXYLATION; DRUG ACTIVITY; DRUG DETERMINATION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION KINETICS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 4043061515     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.059     Document Type: Article

References (39)

1. Otoguro K., Kuno F., Omura S. Pharmacol. Ther. 76:1997;45-54
2. Sugimoto H., Iimura Y., Yamanishi Y., Yamatsu K. J. Med. Chem. 38:1995;4821-4829
3. Ōmura S., Kuno F., Otoguro K., Sunazuka T., Shiomi K., Masuma R., Iwai Y. J. Antibiot. 48:1995;745-746
4. Kuno F., Otoguro K., Shiomi K., Iwai Y., Ōmura S. J. Antibiot. 49:1996;742-747
5. Kuno F., Shiomi K., Otoguro K., Sunazuka T., Ōmura S. J. Antibiot. 49:1996;748-751
6. Otoguro K., Shiomi K., Yamaguchi Y., Arai N., Sunazuka T., Masuma R., Iwai Y., Ōmura S. J. Antibiot. 53:2000;50-57
7. Cornforth J.W. Chem. Ber. 4:1968;102-106
8. Simpson T.J. Chem. Soc. Rev. 16:1987;123-160
9. Handa M., Sunazuka T., Nagai K., Kimura R., Otoguro K., Harigaya Y., Ōmura S. J. Antibiot. 54:2001;386-391
10. Tomoda H., Tabata N., Nakata Y., Nishida H., Kaneko T., Obata R., Sunazuka T., Ōmura S. J. Org. Chem. 61:1996;882-886
11. Ōmura S., Tomoda H., Kim Y.K., Nishida H. J. Antibiot. 46:1993;1168-1169
12. Tomoda H., Kim Y.K., Nishida H., Masuma R., Ōmura S. J. Antibiot. 47:1994;148-153
13. Kim Y.K., Nishida H., Sunazuka T., Obata R., Ōmura S. J. Antibiot. 47:1994;154-162
14. Tomoda H., Nishida H., Kim Y.K., Obata R., Sunazuka T., Ōmura S., Bordner J., Guadllana M., Dormer P.G., Smith A.B. III. J. Am. Chem. Soc. 116:1994;12097-12098
15. Nagamitsu T., Sunazuka T., Obata R., Tomoda H., Tanaka H., Harigaya Y., Ōmura S. J. Org. Chem. 60:1995;8126-8127
16. Otoguro, K.; Wanibuchi, F.; Yamaguchi, T.; Suzuki, K.; Yamaguchi, Y.; Sunazuka, T.; Ōmura, S., unpublished data.
17. Zehnder L.R., Hsung R.P., Wang J., Golding G.M. Angew. Chem., Int. Ed. 39:2000;3876-3879
18. Hua D.H., Chen Y., Sin H.-S., Maroto M.J., Robinson P.D., Newell S.W., Perchellet E.M., Ladesich J.B., Freeman J.A., Perchellet J.-P., Chiang P.K. J. Org. Chem. 62:1997;6888-6896
19. Hsung R.P. J. Org. Chem. 62:1997;7904-7905
20. Hsung R.P., Shen H.C., Douglas C.J., Morgan C.D., Degen S.J., Yao L.J. J. Org. Chem. 64:1999;690-691
21. Cole K.P., Hsung R.P., Yang X.-F. Tetrahedron Lett. 43:2002;3341-3345
22. Hsung R.P., Cole K.P., Zehnder L.R., Wang J., Wei L.-L., Yang X.-F., Coverdale H.A. Tetrahedron. 59:2003;311-324
23. Sunazuka, T.; Nagai, K.; Kimura, R.; Harigaya, Y.; Otoguro, K., Ōmura, S. Abstracts of Papers, 119th Conference Pharmaceutical Society: Japan. (Tokushima, Japan) 1999; pp 2-62.
24. Sunazuka T. J. Synth. Org. Chem. Jpn. 58:2000;828-838
25. Handa M., Sunazuka T., Nagai K., Kimura R., Shirahata T., Tian Z.-M., Otoguro K., Harigaya Y., Ōmura S. J. Antibiot. 54:2001;382-385
26. Preliminary communication: Sunazuka T., Handa M., Nagai K., Shirahata T., Harigaya Y., Otoguro K., Kuwajima I., Ōmura S. Org. Lett. 4:2002;367-369
27. Ohtani I., Kusumi T., Kashman Y., Kakisawa H. J. Org. Chem. 56:1991;1296-1298
28. Dale J.A., Dull D.L., Mosher H.S. J. Org. Chem. 34:1969;2543-2549
29. Delpech B., Calvo D., Lett R. Tetrahedron Lett. 37:1996;1015-1018
30. Nicolaou K.C., Li W.S. J. Chem. Soc., Chem. Commun. 1985;421
31. Corey E.J., Jardine P.D.S., Mohri T. Tetrahedron Lett. 29:1988;6409-6412
32. Calvo D., Port M., Delpech B., Lett R. Tetrahedron Lett. 37:1996;1023-1024
33. Ohkuma T., Doucet H., Pham T., Mikami K., Korenaga T., Terada M., Noyori R. J. Am. Chem. Soc. 120:1998;1086-1087
34. Michaelson R.C., Sharpless K.B. J. Am. Chem. Soc. 95:1973;6136-6137
35. West C.T., Donnelly S.J., Kooistra D.A., Doyle M.P. J. Org. Chem. 38:1973;2675-2681
36. Meyer W.L., Clemans G.B., Manning R.A. J. Org. Chem. 40:1975;3686-3694
37. Nicolaou K.C., Zhong Y.-L., Baran P.S. J. Am. Chem. Soc. 122:2000;7596-7597
38. Ito Y., Hirao T., Saegusa T. J. Org. Chem. 43:1978;1011-1013
39. Peng F.-C. J. Nat. Prod. 58:1995;857-862