Synthesis of (-)-(5R,6S)-6-acetoxyhexadecan-5-olide by L-proline-catalyzed asymmetric aldol reactions

Tetrahedron Asymmetry

Volumn 16, Issue 7, 2005, Pages 1305-1307

  Sun, Bin ^a   Peng, Lizeng ^b   Chen, Xuesong ^a   Li, Yulin ^a   Li, Ying ^a   Yamasaki, Kaori ^c  

^a LANZHOU UNIVERSITY   (China)

^b Lunan Pharmaceutical Co Ltd   (China)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 ACETOXYHEXADECAN 5 OLIDE; ALDEHYDE; CYCLOPENTANONE DERIVATIVE; PHEROMONE DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 26844535228     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.02.017     Document Type: Article

References (26)

1. Laurence, B. R.; Pickett, J. A. J. Chem. Soc., Chem. Commun. 1982, 59.
2. Rieser, M. J.; Koslowski, J. F.; Wood, K. V.; McLaughlin, J. L. Tetrahedron Lett. 1991, 32, 1137.
3. (a) Lin, G. Q.; Xu, H. J.; Wu, B. C.; Guo, G. Z.; Zhou, W. S. Tetrahedron Lett. 1985, 26, 1233;
4. (b) Mori, K.; Otsuka, T. Tetrahedron 1983, 39, 3267;
5. (c) Sato, T.; Watanabe, M.; Honda, N.; Fujisawa, T. Chem. Lett. 1985, 1175;
6. (d) Wu, W. L.; Wu, Y. L. J. Chem. Res. (S) 1990, 112;
7. (e) Lin, G. Q.; Jiang, Y. Y.; Guo, G. Z.; Xia, K. M. Acta Chim. Sinica 1987, 45, 602;
8. (f) Wang, Z. M.; Qian, X. H.; Zhou, W. S. Tetrahedron 1990, 46, 1191;
9. (g) Ramaswamy, S.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1145;
10. (h) Gravier-Pelletier, C.; Saniere, M.; Charvet, I.; Merrer, Y. L.; Depezay, J. C. Tetrahedron Lett. 1994, 35, 115;
11. Coutrot, P. Tetrahedron Lett. 1994, 35, 8381;
12. (j) Bonini, C.; Checconi, M.; Righi, G.; Rossi, L. Tetrahedron 1995, 51, 4111;
13. (k) Figadere, B.; Harmange, J. C.; Laurens, A.; Cave, A. Tetrahedron Lett. 1991, 32, 57539;
14. (l) van Aar, M. P. M.; Thijs, L.; Zwanenburg, B. Tetrahedron 1995, 41, 11223;
15. Somfai, P. J. Chem. Soc., Perkin Trans. 1 1995, 817.
16. Peng, L. Z.; Liu, H. W.; Zhang, T.; Zhang, F. Z.; Mei, T. S.; Li, Y.; Li, Y. L. Tetrahedron Lett. 2003, 44, 5107.
17. (a) List, B.; Pojarliev, P.; Biller, W. T.; Martin, H. J. J. Am. Chem. Soc. 2002, 124, 827;
18. (b) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395;
19. (c) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573;
20. (d) List, B. Tetrahedron 2002, 58, 5573;
21. (e) List, B. Synlett 2001, 11, 1675;
22. (f) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260;
23. (g) for reviews and highlights of the proline-catalyzed direct asymmetric aldol reaction in various contexts, see: Gröger, H.; Wilken, J. Angew. Chem., Int. Ed. 2001, 40, 529;
24. (h) Palomo, C.; Oiarbide, M.; Garcia, J. M. Chem. Eur. J. 2001, 8, 37;
25. (i) Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2002, 67, 1595;
26. (j) Movassaghi, M.; Jacobsen, E. N. Science 2002, 298, 1904.