A facile asymmetric synthesis of (+)-eldanolide

Tetrahedron Asymmetry

Volumn 18, Issue 4, 2007, Pages 451-454

  Kong, Linglong ^a,c   Zhuang, Zeyang ^a,c   Chen, Qingshou ^a   Deng, Haibing ^a   Tang, Zhiyong ^b,d   Jia, Xueshun ^c   Li, Yulin ^d   Zhai, Hongbin ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^c SHANGHAI UNIVERSITY   (China)

^d LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ELDANOLIDE; EPOXIDE; LACTONE DERIVATIVE; SEX PHEROMONE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; EPOXIDATION; HORMONE SYNTHESIS; LACTONIZATION; PRIORITY JOURNAL; SAPONIFICATION;

EID: 33947279305     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.01.035     Document Type: Article

References (33)

1. Kunesch G., Zagatti P., Lallemand J.Y., Debal A., and Vigneron J.P. Tetrahedron Lett. 22 (1981) 5271-5274
2. Vigneron J.P., Meric R., Larcheveque M., Debal A., Lallemand J.Y., Kunesch G., Zagatti P., and Gallois M. Tetrahedron 40 (1984) 3521-3529
3. For representative synthesis of eldanolide since 1991, see:. Villar F., Kolly-Kovac T., Equey O., and Renaud P. Chem. Eur. J. 9 (2003) 1566-1577
4. Villar F., Equey O., and Renaud P. Org. Lett. 2 (2000) 1061-1064
5. Angert H., Czerwonka R., and Reissig H.U. Liebigs Ann. 2 (1996) 259-263
6. Xu Z.-H., Huang J.-X., Li Y., Chen Z.-X., and Gao M.-Z. Chem. J. Chin. Univ. 16 (1995) 1391-1395
7. Hondo T., Yamane S., Naito K., and Suzuki Y. Heterocycles 37 (1994) 515-521
8. Mobbili G., Orena M., Porzi G., and Sandri S. J. Chem. Res., Synop. 6 (1993) 230-231
9. Paulsen H., and Hoppe D. Tetrahedron 48 (1992) 5667-5670
10. Suzuki Y., Mori W., Ishizone H., Naito K., and Honda T. Tetrahedron Lett. 33 (1992) 4931-4932
11. Herradon B. Tetrahedron: Asymmetry 2 (1991) 191-194
12. For representative synthesis of eldanolide before 1990, see:. Bloch R., and Seck M. Tetrahedron 45 (1989) 3731-3740
13. Yadav J.S., and Gadgil V.R. J. Chem. Soc., Chem. Commun. (1989) 1824-1825
14. Ortuno R.M., Merce R., and Font J. Tetrahedron Lett. 27 (1986) 2519-2522
15. Davies H.G., Roberts S.M., Wakefield B.J., and Winders J.A. J. Chem. Soc., Chem. Commun. (1985) 1166-1168
16. Suzuki K., Ohkuma T., and Tsuchihashi G. Tetrahedron Lett. 26 (1985) 861-864
17. Uematsu T., Umemura T., and Mori K. Agric. Biol. Chem. 47 (1983) 597-601
18. Vigneron J.P., Meric R., Larcheveque M., Debal A., Kunesch G., Zagatti P., and Gallois M. Tetrahedron Lett. 23 (1982) 5051-5054
19. For Sharpless asymmetric epoxidation, see:. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974-5976
20. For ring opening of 2,3-epoxy alcohols, see:. Lin G.-Q., Li Y.-M., and Chan A.S.C. Principle and Application of Asymmetric Synthesis (2001), Wiley Interscience, New York
21. Johnson M.R. Tetrahedron Lett. 45 (1979) 4343-4346
22. Mori K., and Itou M. Liebigs Ann. Chem. 1 (1992) 87-93
23. Nakamura R., Tanino K., and Miyashita M. Org. Lett. 5 (2003) 3579-3582
24. Ren X.F., Konaklieva M.K., Turos E., Krajkowski L.M., Lake C.H., Janik T.S., and Churchill M.R. J. Org. Chem. 60 (1995) 6484-6495
25. Davies S.G., and Ichihara O. Tetrahedron Lett. 40 (1999) 9313-9316
26. Yadav J.S., Praveen Kumar T.K., and Maniyan P.P. Tetrahedron Lett. 34 (1993) 2965-2968
27. Andrey O., Glanzmann C., Landais Y., and Parra-Rapado L. Tetrahedron 53 (1997) 2835-2854
28. Yadav J.S., Deshpande P.K., and Sharma G.V. Tetrahedron 46 (1990) 7033-7046
29. 10c
30. Watanabe H., Bando M., Kido M., and Kitahara T. Tetrahedron 55 (1999) 9755-9776
31. Ziegler F.E., and Wang Y. Tetrahedron Lett. 37 (1996) 6299-6302
32. For an example of one carbon elongation and subsequent transformations, see:. Wu Y.K., Shen X., Tang C.J., Chen Z.L., Hu Q., and Shi W. J. Org. Chem. 67 (2002) 3802-3810
33. See Section 4.