A stereoselective synthesis of (4E,7S)-(-)-7-methoxydodec-4-enoic acid

Synthesis

Volumn , Issue 2, 2006, Pages 320-324

  Li, Yang ^a   Chen, Jie ^a   Cao, Xiao Ping ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

(4E,7S) ( ) 7 methoxydodec 4 enoic acid; Catalytic asymmetric allylation; Coupling reaction; Stereoselective synthesis

Indexed keywords

ALDEHYDES; CATALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CATALYTIC ASYMMETRIC ALLYLATION; COUPLING REACTION; STEREOSELECTIVE SYNTHESIS;

CARBOXYLIC ACIDS;

7 METHOXYDODEC 4 ENOIC ACID; ALKYNE DERIVATIVE; BROMIDE; HEXANAL; LAURIC ACID DERIVATIVE; LITHIUM DERIVATIVE; TERT BUTYLLITHIUM; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CHIRALITY; CROSS COUPLING REACTION; QUANTUM YIELD; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 31544446623     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918516     Document Type: Article

References (38)

1. (a) Cardellina, J. H. II.; Dalietos, D.; Marner, F. J.; Mynderse, J. S.; Moore, R. E. Phytochemistry 1978, 17, 2091.
2. (b) Mynderse, J. S.; Moore, R. E. J. Org. Chem. 1978, 43, 4359.
3. (c) Cardellina, J. H. II.; Marner, F. J.; Moore, R. E. J. Am. Chem. Soc. 1979, 101, 240.
4. (d) Ainslie, R. D.; Barchi, J. J.; Kuniyoshi, M.; Moore, R. E.; Mynderse, J. S. J. Org. Chem. 1985, 50, 2859.
5. (e) Gerwick, W. H.; Reyes, S.; Alvarado, B. Phytochemistry 1987, 26, 1701.
6. (f) Praud, A.; Valls, R.; Piovetti, L.; Banaigs, B. Tetrahedron Lett. 1993, 34, 5437.
7. (g) Orjala, J.; Nagle, D.; Gerwick, W. H. J. Nat. Prod. 1995, 58, 764.
8. (h) Todd, J. S.; Gerwick, W. H. Tetrahedron Lett. 1995, 36, 7837.
9. (i) Wu, M.; Milligan, K. E.; Gerwick, W. H. Tetrahedron 1997, 53, 15983.
10. (j) Kan, Y.; Fujita, T.; Nagai, H.; Sakamoto, B.; Hokama, Y. J. Nat. Prod. 1998, 61, 152.
11. (k) Wan, F.; Erickson, K. L. J. Nat. Prod. 1999, 62, 1696.
12. (l) Tan, L. T.; Okino, T.; Gerwick, W. H. J. Nat. Prod. 2000, 63, 952.
13. (m) Milligan, K. E.; Marquez, B.; Williamson, R. T.; Davies-Coleman, M.; Gerwick, W. H. J. Nat. Prod. 2000, 63, 965.
14. (n) Gallimore, W. A.; Scheuer, P. J. J. Nat. Prod. 2000, 63, 1422.
15. (o) Kan, Y.; Sakamoto, B.; Fujita, T.; Nagai, H. J. Nat Prod. 2000, 63, 1599.
16. (p) Appleton, D. R.; Sewell, M. A.; Berridge, M. V.; Copp, B. R. J. Nat. Prod. 2002, 65, 630.
17. (q) McPhail, K. L.; Gerwick, W. H. J. Nat. Prod. 2003, 66, 132.
18. (r) Nogle, L. M.; Gerwick, W. H. J. Nat. Prod. 2003, 66, 217.
19. (a) Fryhle, C. B.; Williard, P. G.; Rybak, C. M. Tetrahedron Lett. 1992, 33, 2327.
20. (b) Muller, C.; Voss, G.; Gerlach, H. Liebigs Ann. Chem. 1995, 673.
21. (c) Sankaranarayanan, S.; Sharma, A.; Chattopadhyay, S. Tetrahedron: Asymmetry 1996, 7, 2639.
22. (d) Mesguiche, V.; Valls, R.; Piovetti, L.; Peiffer, G. Tetrahedron Lett. 1999, 40, 7473.
23. (a) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001.
24. (b) Hanawa, H.; Hashimoto, T.; Maruoka, K. J. Am. Chem. Soc. 2003, 125, 1708.
25. (c) Gupta, P.; Naidu, S. V.; Kumar, P. Tetrahedron Lett. 2004, 45, 849.
26. Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788.
27. (a) Adkins, H.; Burks, R. E. Org. Synth. 1947, 27, 76.
28. (b) Campbell, K. N.; Campbell, B. K. Org. Synth. 1950, 30, 72.
29. Harris, G. D.; Herr, R. J.; Weinreb, S. M. J. Org. Chem. 1993, 58, 5452.
30. (a) Bauld, N. L.; Harirchian, B.; Reynolds, D. W.; White, J. C. J. Am. Chem. Soc. 1988, 110, 8111.
31. (b) Kulkarni, B. A.; Chattopadhyay, S.; Chattopadhyay, A.; Mamdapur, V. R. J. Org. Chem. 1993, 58, 5964.
32. Doolittle, R. E.; Patrick, D. G.; Heath, R. H. J. Org. Chem. 1993, 58, 5063.
33. Miyashita, N.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
34. Cao, X.; Yang, Y.; Wang, X. J. Chem. Soc., Perkin Trans. 1 2002, 2485.
35. Lane, J. W.; Halcomb, R. L. Org. Lett. 2003, 5, 4017.
36. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 36, 3769.
37. t-BuLi it is not commercially available to us due to transportation problems.
38. No other signals were observed around the chiral center (C-7 and C-1′).