Total synthesis of (±)-carquinostatin A, and asymmetric total synthesis of (R)-(-)-carquinostatin A and (S )-(+)-carquinostatin A

Chemical and Pharmaceutical Bulletin

Volumn 60, Issue 12, 2012, Pages 1522-1530

  Hieda, Yuhzo ^a   Choshi, Tominari ^a   Uchida, Yoshinari ^a   Fujioka, Haruto ^a   Fujii, Sayuri ^a   Hibino, Satoshi ^a  

^a FUKUYAMA UNIVERSITY   (Japan)

Author keywords

( ) carquinostatin A; (R) ( ) carquinostatin A; (S ) (+) carquinostatin A; Asymmetric synthesis; Lipase QLM; Total synthesis

Indexed keywords

1 (2 ACETOXYPROPYL) 3 HYDROXY 2 METHYL 6 PRENYLCARBAZOLE; 1 (2 ACETOXYPROPYL) 3 HYDROXY 2 METHYLCARBAZOLE; 1 (2 ACETOXYPROPYL) 6 BROMO 3 HYDROXY 2 METHYLCARBAZOLE; 1 ACETONYL 3 ETHOXY 2 METHYLCARBAZOLE; 1 ACETONYL 6 BROMO 3 ETHOXY 2 METHYLCARBAZOLE; 1 ACETONYLCARBAZOLE; 3 ACETOXY 1 (2 ACETOXYPROPYL) 2 METHYL 6 PRENYLCARBAZOLE; 3 ACETOXY 1 (2 ACETOXYPROPYL) 6 ALLYL 2 METHYLCARBAZOLE; 3 ACETOXY 1 (2 ACETOXYPROPYL) 6 BROMO 2 METHYLCARBAZOLE; 3 HYDROXY 1 (2 HYDROXYPROPYL) 2 METHYL 6 PRENYLCARBAZOLE; 3 HYDROXY 1 (2 HYDROXYPROPYL) 2 METHYLCARBAZOLE; 6 BROMO 3 HYDROXY 1 (2 HYDROXYPROPYL) 2 METHYLCARBAZOLE; ANTIOXIDANT; CARBAZOLE DERIVATIVE; CARQUINOSTATIN A; LAVANDUQUINOCIN; N BROMOSUCCINIMIDE; NEOCARQUINOSTATIN B; STREPTVERTICILLIN; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHIRALITY; CROSS COUPLING REACTION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; TRANSESTERIFICATION;

CARBAZOLES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84871216466     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.c12-00650     Document Type: Article

References (33)

1. Shin-ya K., Tanaka M., Furihata K., Hayakawa Y., Seto H., Tetrahedron Lett., 34, 4943-4944 (1993).
2. Orihara N., Furihata K., Seto H., J. Antibiot., 50, 979-981 (1997).
3. Shin-ya K., Kunigami T., Kim J.-S., Furihata K., Hayakawa Y., Seto H., Biosci. Biotechnol. Biochem., 61, 1768-1769 (1997).
4. Schmidt A. W., Reddy K. R., Knölker H.-J., Chem. Rev., 112, 3193-3328 (2012).
5. Bauer I., Knölker H.-J., Top. Curr. Chem., 309, 203-253 (2012).
6. Forke R., Gruner K. K., Knott K. E., Auschill S., Agarwal S., Martin R., Böhl M., Richter S., Tsiavaliaris G., Fedorov R., Manstein D. J., Gutzeit H. O., Knölker H.-J., Pure Appl. Chem., 82, 1975-1991 (2010).
7. Knölker H.-J., Top. Curr. Chem., 244, 115-148 (2005).
8. Chakraborty D. P., Roy S., "Progress in the Chemistry of Organic Natural Products," ed. by Herz W., Grisebach H., Kirby G. W., Steglich W., Tamm C., Springer-Verlag, Wien, 2003, pp. 128-230.
9. Knölker H.-J., Reddy K. R., Chem. Rev., 102, 4303-4427 (2002).
10. Knölker H.-J., Fröhner W., Synlett, 1997, 1108-1110 (1997).
11. Fröhner W., Reddy K. R., Knölker H.-J., Heterocycles, 74, 895-912 (2007).
12. Knölker H.-J., Reddy K. R., Synlett, 1999, 596-598 (1999).
13. Knölker H.-J., Baum E., Reddy K. R., Tetrahedron Lett., 41, 1171-1174 (2000).
14. Knölker H.-J., Fröhner W., Tetrahedron Lett., 39, 2537-2540 (1998).
15. Fröhner W., Reddy K. R., Knölker H.-J., ARKIVOC, 2012, 330-342 (2012).
16. Czerwonka R., Reddy K. R., Baum E., Knölker H.-J., Chem. Commun. (Camb.), 2006, 711-713 (2006).
17. Thomas C., Kataeva O., Knölker H.-J., Synlett, 2011, 2663-2666 (2011).
18. Choshi T., Hibino S., Heterocycles, 83, 1205-1239 (2011).
19. Choshi T., Hibino S., Heterocycles, 77, 85-97 (2009).
20. Choshi T., Sada T., Fujimoto H., Nagayama C., Sugino E., Hibino S., Tetrahedron Lett., 99, 2593-2596 (1996).
21. Choshi T., Sada T., Fujimoto H., Nagayama C., Sugino E., Hibino S., J. Org. Chem., 62, 2535-2543 (1997).
22. Choshi T., Fujimoto H., Sugino E., Hibino S., Heterocycles, 43, 1847-1854 (1996).
23. Hagiwara H., Choshi T., Fujimoto H., Sugino E., Hibino S., Chem. Pharm. Bull., 46, 1948-1949 (1998).
24. Hagiwara H., Choshi T., Fujimoto H., Sugino E., Hibino S., Tetrahedron, 56, 5807-5811 (2000).
25. Hagiwara H., Choshi T., Nobuhiro J., Fujimoto H., Hibino S., Chem. Pharm. Bull., 49, 881-886 (2001).
26. Tohyama S., Choshi T., Matsumoto A., Yamabuki A., Ikegata K., Nobuhiro J., Hibino S., Tetrahedron Lett., 46, 5263-5264 (2005).
27. Yamabuki A., Fujinawa H., Choshi T., Tohyama S., Matsumoto K., Ohmura K., Nobuhiro J., Hibino S., Tetrahedron Lett., 47, 5859-5861 (2006).
28. Tohyama S., Choshi T., Azuma S., Fujioka H., Hibino S., Heterocycles, 79, 955-965 (2009).
29. Tohyama S., Choshi T., Matsumoto K., Yamabuki A., Hieda Y., Nobuhiro J., Hibino S., Heterocycles, 82, 397-416 (2010).
30. Hieda Y., Choshi T., Kishida S., Fujioka H., Hibino S., Tetrahedron Lett., 51, 3593-3596 (2010).
31. Choshi T., Uchida Y., Kubota Y., Nobuhiro J., Takeshita M., Hatano T., Hibino S., Chem. Pharm. Bull., 55, 1060-1064 (2007).
32. Harada N., Watanabe M., Kuwahara S., Sugino A., Kasai Y., Ichikawa A., Tetrahedron Asymmetry, 11, 1249-1253 (2000).
33. Tsuji H., Kasai Y., Sugino A., Kuwahara S., Watanabe M., Harada N., Ichikawa A., Chirality, 14, 81-84 (2002).