Synthetic studies on (+)-biotin, part 151: A chiral squaramide-mediated enantioselective alcoholysis approach toward the total synthesis of (+)-biotin

Chemical and Pharmaceutical Bulletin

Volumn 59, Issue 4, 2011, Pages 488-491

  Chen, Xu Xiang ^a   Xiong, Fei ^a   Fu, Han ^a   Liu, Zhi Qian ^a   Chen, Fen Er ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

(+) biotin; Cinchona alkaloid derived squaramide; Enantioselective alcoholysis; Tricyclic thiophanium salt

Indexed keywords

1,3 DIBENZYL 2 IMIDAZOLE 4,5 DICARBOXYLIC ACID; BIOTIN; CARBOXYLIC ACID; CINCHONA ALKALOID; IMIDAZOLE; SQUARAMIDE; UNCLASSIFIED DRUG;

ALCOHOLYSIS; ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MOLECULAR INTERACTION; STRUCTURE ACTIVITY RELATION;

AMIDES; BIOTIN; DICARBOXYLIC ACIDS; STEREOISOMERISM;

EID: 79953656017     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.59.488     Document Type: Article

References (27)

1. Xiong F., Chen X. X., Liu Z. Q., Chen F. E., Tetrahedron Lett., 51, 3670-3672 (2010).
2. Atodiresei I., Schiffers I., Bolm C., Chem. Rev., 107, 5683-5712 (2007).
3. Chen Y. G., Mcdaid P., Deng L., Chem. Rev., 103, 2965-2983 (2003).
4. Spivey A. C., Andrews B. I., Angew. Chem. Int. Ed., 40, 3131-3134 (2001).
5. Peschiulli A., Gun'ko Y., Connon S. J., J. Org. Chem., 73, 2454-2457 (2008).
6. Rho H. S., Oh S. H., Lee J. W., Lee J. Y., Chin J., Song C. E., Chem. Commun., 2008, 1208-1210 (2008).
7. Oh S. H., Rho H. S., Lee J. W., Lee J. E., Youk S. H., Chin J., Song C. E., Angew. Chem. Int. Ed., 47, 7872-7875 (2008).
8. Wang S. X., Chen F. E., Adv. Synth. Catal., 351, 547-552 (2009).
9. Youk S. H., Oh S. H., Rho H. S., Lee J. E., Lee J. W., Song C. E., Chem. Commun., 2009, 2220-2222 (2009).
10. Schmitt E., Schiffers I., Bolm C., Tetrahedron, 66, 6349-6357 (2010).
11. Wakchaure V. N., List B., Angew. Chem. Int. Ed., 49, 4136-4139 (2010).
12. Manzano R., Andres J. M., Muruzabal M. D., Pedrosa R., J. Org. Chem., 75, 5417-5420 (2010).
13. Honjo T., Tsumura T., Sano S., Nagao Y., Yamaguchi K., Sei Y., Synlett, 20, 3279-3282 (2009).
14. Hiratake J., Yamamoto Y., Oda J., J. Chem. Soc. Chem. Commun., 1985, 1717-1719 (1985).
15. Hiratake J., Inagaki M., Yamamoto Y., Oda J., J. Chem. Soc. Perkin Trans. 1, 1987, 1053-1058 (1987).
16. Huang J., Xiong F., Chen F. E., Tetrahedron: Asymmetry, 19, 1436-1443 (2008).
17. Xiong F., Chen X. X., Chen F. E., Tetrahedron: Asymmetry, 21, 665-669 (2010).
18. De Clercq P. J., Chem. Rev., 97, 1755-1792 (1997).
19. Seki M., Med. Res. Rev., 26, 434-482 (2006).
20. Dai L., Wang S. X., Chen F. E., Adv. Synth. Catal., 352, 2137-2141 (2010).
21. Chen F. E., Chen X. X., Dai H. F., Kuang Y. Y., Xie B., Zhao J. F., Adv. Synth. Catal., 347, 549-554 (2005).
22. Hu M. G., Chen J., Chen F. E., Chen J. W., Chin. J. Pharm., 22, 461-462 (2006).
23. Chen F. E., Yuan J. L., Dai H. F., Kuang Y. Y., Chu Y., Synthesis, 2003, 2155-2160 (2003).
24. Dai H. F., Chen W. X., Zhao L., Xiong F., Sheng H., Chen F. E., Adv. Synth. Catal., 350, 1635-1641 (2008).
25. Armarego W. L. F., Chai C., "Purification of Laboratory Chemicals," Butterworth Heinemann, Oxford, 2003.
26. Chen F. E., Dai H. F., Kuang Y. Y., Jia H. Q., Tetrahedron: Asymmetry, 14, 3667-3672 (2003).
27. Chen F. E., Yuan J. L., Dai H. F., Kuang Y. Y., Chu Y., Synthesis, 2000, 2004-2008 (2000).