An efficient synthesis of the CD rings model for merrilactone A

Tetrahedron Letters

Volumn 48, Issue 35, 2007, Pages 6105-6108

  Harada, Kenichi ^a   Ito, Hitoshi ^a   Hioki, Hideaki ^a   Fukuyama, Yoshiyasu ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

1,1 Dibromo 1 alkene; Merrilactone A; Miyashita's protocol; Tsuji Trost reaction

Indexed keywords

GAMMA LACTONE DERIVATIVE; LACTONE DERIVATIVE; MERRILACTONE A; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMICAL REACTION; HECK REACTION; METHYLATION; MIZOROKI REACTION; STILLE REACTION; SYNTHESIS; TSUJI TROST REACTION;

EID: 34547486972     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.06.159     Document Type: Article

References (25)

1. Huang J.-M., Yokoyama R., Yang C.-S., and Fukuyama Y. Tetrahedron Lett. 41 (2000) 6111-6114
2. Huang J.-M., Yang C.S., Tanaka M., and Fukuyama Y. Tetrahedron 57 (2001) 4691-4698
3. Synthetic studies on merrilactone A:. Hong B.-C., Shr T.-J., Wu J.-L., Gupta A.K., and Lin K.-J. Org. Lett. 4 (2002) 2249-2252
4. Metha G., and Sigh S.R. Tetrahedron Lett. 46 (2005) 2079-2082
5. Irionodo-Alberdi J., Perea-Buceta J.E., and Greney M.F. Org. Lett. 7 (2005) 3969-3971
6. Birman V.B., and Danishefsky S.J. J. Am. Chem. Soc. 124 (2002) 2080-2081
7. Inoue M., Sato T., and Hirama M. J. Am. Chem. Soc. 125 (2003) 10772-10773
8. Mehta G., and Singh S.R. Angew. Chem., Int. Ed. 45 (2006) 953-955
9. He W., Huang J., Sun X., and Frontier A.J. J. Am. Chem. Soc. 129 (2007) 498-499
10. The asymmetric synthesis of 1:. Meng Z., and Danishefsky S.J. Angew. Chem., Int. Ed. 44 (2005) 1511-1513
11. Inoue M., Sato T., and Hirama M. Angew. Chem., Int. Ed. 45 (2006) 4843-4848
12. Inoue M., Lee N., Kasuya S., Sato T., Hirama M., Moriyama M., and Fukuyama Y. J. Org. Chem. 72 (2007) 3065-3975
13. Harada K., Kato H., and Fukuyama Y. Tetrahedron Lett. 46 (2005) 7407-7410
14. Tsuji J., Takahashi H., and Morikawa M. Tetrahedron Lett. 6 (1965) 4387-4388
15. Tanino K., Arakawa K., Satoh M., Iwata Y., and Miyashita M. Tetrahedron Lett. 47 (2006) 861-864
16. Corey E.J., and Fuchs P.L. Tetrahedron Lett. 13 (1972) 3769-3772
17. 4. Evaporation and purification by column chromatography (silica gel, hexane:AcOEt = 9:1) gave 9a (21.7 mg, 78% yield).
18. Fournier-Nguefack C., Lhoste P., and Sinou D. Tetrahedron 53 (1997) 4353-4362
19. -1): 1793.
20. Milstein D., and Stille J.K. J. Am. Chem. Soc. 101 (1979) 4992-4998
21. Evans D.A., and Starr J.T. Angew. Chem., Int. Ed. 41 (2002) 1787-1790
22. Negishi E. Pure. Appl. Chem. 53 (1981) 2333-2356
23. Hayashi T., Konishi M., Okamoto Y., Kabeta K., and Kumada M. J. Org. Chem. 51 (1986) 3772-3781
24. -1): 1769.
25. -1): 3415, 1732.