Asymmetric total synthesis of (+)-curcutetraol and (+)-sydonol

Tetrahedron

Volumn 64, Issue 42, 2008, Pages 9879-9884

  Ito, Suguru ^a   Zhang, Chenxia ^a   Hosoda, Naoya ^a   Asami, Masatoshi ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

Asymmetric total synthesis; Curcutetraol; Sesquiterpene; Sydonol

Indexed keywords

2 METHOXYCARBONYL 3 PHENYL 1,3 DIAZABICYCLO[3.3.0]OCTANE; ALDEHYDE DERIVATIVE; BENZYL ALCOHOL; CURCUTETRAOL; OCTANE; PHENOL DERIVATIVE; SESQUITERPENOID; SYDONOL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 50549101061     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.012     Document Type: Article

References (43)

1. Wright A.E., Pomponi S.A., McConnell O.J., Kohmoto S., and McCarthy P.J. J. Nat. Prod. 50 (1987) 976-978
2. Fusetani N., Sugano M., Matsunaga S., and Hashimoto K. Experientia 43 (1987) 1234-1235
3. Butler M.S., Capon R.J., Nadeson R., and Beveridge A.A. J. Nat. Prod. 54 (1991) 619-623
4. El Sayed K.A., Yousaf M., Hamann M.T., Avery M.A., Kelly M., and Wipf P. J. Nat. Prod. 65 (2002) 1547-1553
5. Peng J., Franzblau S.G., Zhang F., and Hamann M.T. Tetrahedron Lett. 43 (2002) 9699-9702
6. Tasdemir D., Bugni T.S., Mangalindan G.C., Concepcion G.P., Harper M.K., and Ireland C.M. Turk. J. Chem. 27 (2003) 273-279
7. McEnroe F.J., and Fenical W. Tetrahedron 34 (1978) 1661-1664
8. Bohlmann F., and Lonitz M. Chem. Ber. 111 (1978) 843-852
9. Ghisalberti E.L., Jefferies P.R., and Stuart A.D. Aust. J. Chem. 32 (1979) 1627-1630
10. D'Armas H.T., Mootoo B.S., and Reynolds W.F. J. Nat. Prod. 63 (2000) 1593-1595
11. Gul W., Hammond N.L., Yousaf M., Peng J., Holley A., and Hamann M.T. Biochim. Biophys. Acta 1770 (2007) 1513-1519
12. Takamatsu S., Hodges T., Rajbhandari I., Gerwick W., Hamann M., and Nagle D. J. Nat. Prod. 66 (2003) 605-608
13. Imai S., Morikiyo M., Furihata K., Hayakawa Y., and Seto H. Agric. Biol. Chem. 54 (1990) 2367-2371
14. Nanba, R.; Isozaki, M.; Endo, I.; Yomo, Y. Jpn. Kokai Tokkyo Koho, Jpn. Pat. Appl. JP 89-60236 19890313;
15. Chem. Abstr. 114 (1990) 121718
16. Aguilar M., and Delgado G. Nat. Prod. Lett. 7 (1995) 155-162
17. Aguilar M.I., Delgado G., Hernanadez M., and Villarreal M.L. Nat. Prod. Lett. 15 (2001) 93-101
18. Kim S., Hong K., Chung W., Hwang J., and Park K. Toxicol. Appl. Pharmacol. 196 (2004) 346-355
19. Mülhaupt T., Kaspar H., Otto S., Reichert M., Bringmann G., and Lindel T. Eur. J. Org. Chem. (2005) 334-341
20. Nukina M., Sato Y., Ikeda M., and Sassa T. Agric. Biol. Chem. 45 (1981) 789-790
21. Hamasaki T., Nagayama K., and Hatsuda Y. Agric. Biol. Chem. 42 (1978) 37-40
22. Henne P., Thiericke R., Grabley S., Hütter K., Wink J., Jurkiewicz E., and Zeeck A. Liebigs Ann. Chem. (1993) 565-571
23. Zeeck, A.; Henne, P.; Grabley, S.; Wink, J; Hutter, K.; Thiericke, R.; Haenel, H. Ger. Offen. DE 4231451, 1994;
24. Chem. Abstr. 121 (1994) 7444
25. Yu D.Q., Xie F.Z., Chen Y., and Huang Y.H. Chin. Chem. Lett. 7 (1996) 721-722
26. Fuganti C., and Serra S. J. Chem. Soc., Perkin Trans. 1 (2000) 3758-3764
27. Ono M., Ogura Y., Hatogai K., and Akita H. Chem. Pharm. Bull. 12 (2001) 1581-1585
28. Kimachi T., and Takemoto Y. J. Org. Chem. 66 (2001) 2700-2704
29. Singh V., Khurana A., Kaur I., Sapehiyia V., Kad G., and Singh J. J. Chem. Soc., Perkin Trans. 1 (2002) 1766-1768
30. Harmata M., Hong X., and Barnes C. Tetrahedron Lett. 44 (2003) 7261-7264
31. Lu J., Xie X., Chen B., She X., and Pan X. Tetrahedron: Asymmetry 16 (2005) 1435-1438
32. Kim S.G., Kim J., and Jung H. Tetrahedron Lett. 46 (2005) 2437-2439
33. Kamal A., Malik M.S., Shaik A.A., and Azeeza S. Tetrahedron: Asymmetry 18 (2007) 2547-2553
34. Zhang C., Ito S., Hosoda N., and Asami M. Tetrahedron Lett. 49 (2008) 2552-2554
35. Mukaiyama T., Sakito Y., and Asami M. Chem. Lett. (1979) 705-708
36. Miyazaki H., Honda K., Asami M., and Inoue S. J. Org. Chem. 64 (1999) 9507-9511
37. Buehler C.A., Harris J.O., Shacklett C., and Block B.P. J. Am. Chem. Soc. 68 (1946) 574-577
38. Canceill J., and Collet A. New J. Chem. 10 (1986) 17-23
39. Taber D.F., and Joerger J.-M. J. Org. Chem. 72 (2007) 3454-3457
40. Fall Y., Vitale C., and Mouriño A. Tetrahedron Lett. 41 (2000) 7337-7340
41. Andrews D.R., Barton D.H.R., Hesse R.H., and Pechet M.M. J. Org. Chem. 51 (1986) 4819-4828
42. Lipshutz B.H., and Miller T.A. Tetrahedron Lett. 30 (1989) 7149-7152
43. Kan T., Hashimoto M., Yanagiya M., and Shirahama H. Tetrahedron Lett. 29 (1988) 5417-5418