Asymmetric total synthesis of (-)-cladospolide B

Chinese Journal of Chemistry

Volumn 26, Issue 6, 2008, Pages 1109-1113

  Wang, Wen Kuan ^a   Zhang, Ji Yong ^a   He, Jin Mei ^a   Tang, Shi Bing ^a   Wang, Xiao Lei ^a   She, Xue Gong ^a,b   Pan, Xin Fu ^a  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

( ) cladospolide B; Mitsunobu esterification; Ring closing metathesis; Sharpless asymmetric dihydroxylation

Indexed keywords

EID: 49149097691     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200890197     Document Type: Article

References (23)

1. Hirota, A.; Sakai, H.; Isogai, A. Agric Biol. Chem. 1985, 49, 731.
2. Smith, C. J.; Abbanat, D.; Bernan, V. S.; Maiese, W. M.; Greenstein, M.; Jompa, J.; Tahir, A.; Ireland, C. M. J. Nat. Prod. 2000, 63, 142.
3. Fuji, Y.; Fukuda, A.; Hamasaki, T.; Ichimoto, I.; Nakajima, H. Phytochemistry 1995, 40, 1443.
4. (a) Austin, K. A. B.; Banwell, M. G.; Loong, D. T. J.; David Rae, A.; Willis, A. C. Org. Biomol. Chem. 2005, 3, 1081.
5. (b) Pandey, S. K.; Kumar, P. Tetrahedron Lett. 2005, 46, 6625.
6. (c) Sharma, G. V. M.; Reddy, K. L.; Reddy, J. J. Tetrahedron Lett. 2006, 47, 6531.
7. (d) Sharma, G. V. M.; Reddy, K. L.; Reddy, J. J. Tetrahedron Lett. 2006, 47, 6537.
8. (a) Lu, J.; Ma, J.; Xie, X.; Chen, B.; She, X.; Pan, X. Tetrahedron: Asymmetry 2006, 17, 1066.
9. (b) Liang, Q.; Zhang, J.; Quan, W.; Sun, Y.; She, X.; Pan, X. J. Org. Chem. 2007, 72, 2694.
10. (c) Liang, Q.; Sun, Y.; Yu, B.; She, X.; Pan, X. J. Org. Chem. 2007, 72, 9846.
11. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
12. (b) Chatterjee, A. K.; Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc. 2000, 122, 3783.
13. (c) Trnka, T.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
14. (a) Becker, H.; Sharpless, K. B. Angew Chem., Int. Ed. Engl. 1996, 35, 448.
15. (b) Kolb, H. C.; VanNiwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
16. Yang, Y.-Q.; Wu, Y.-K. Chin. J. Chem. 2005, 23, 1519.
17. Tsuda, Y.; Hosoi, H. S.; Goto, Y. Chem. Pharm. Bull. 1991, 39, 18.
18. Mancuso, A. J.; Huang, S. L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
19. McKenna, C. E.; Khawli, L. A. J. Org. Chem. 1986, 51, 5467.
20. Ando, K. J. Org. Chem. 1997, 62, 1934.
21. For the measurement of enantiomeric excess, the diol 9 was converted into its dibenzoate. The enantiomeric purity of the dibenzoate was estimated to be 99% by chiral HPLC using Varian Dynamax SD-300 via a chiralcel column CDMPC (150 mm X 4.6 mm φ 1% i-PrOH in hexane, rate 0.7 mL/min).
22. Shen, Y. C.; Qiu, W. M. Synthesis 1987, 42.
23. Mitsunobu, O. Synthesis 1981, 1.