A novel total synthesis of kinsenoside and goodyeroside A relying on the efficient reaction of the chiral 2(5H)-furanones

Journal of Asian Natural Products Research

Volumn 7, Issue 5, 2005, Pages 711-721

  Zhang, Xiang ^a   Huang, Hai Hong ^a   Chen, Qing Hun ^b  

^a INSTITUTE OF MATERIA MEDICA   (China)

^b BEIJING NORMAL UNIVERSITY   (China)

Author keywords

Goodyeroside A; Kinsenoside; Total synthesis

Indexed keywords

4 O ( BETA DEXTRO GLUCOPYRANOSYL) 2(5H) FURANONE; FURANONE DERIVATIVE; GLYCOSIDE; GOODYEROSIDE A; KINSENOSIDE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; GLYCOSIDATION; SPECTROSCOPY; STEREOCHEMISTRY;

FURANS; MOLECULAR STRUCTURE; MONOSACCHARIDES; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 26044438842     PISSN: 10286020     EISSN: 14772213     Source Type: Journal    
DOI: 10.1080/1028602042000324916     Document Type: Article

References (24)

1. A. Ito, R. Kasai, K. Yamasaki, H. Sugimoto. Phytochemistry, 33, 1133 (1993).
2. X.M. Du, T. Yoshizawa, Y. Shoyama. Phytochemistry, 49, 1925 (1998).
3. Z.C. Sun. Harvest Farm Magazine (Taiwan) in The Herbs, p. 57 (1987).
4. W.Y. Gao, Y.M. Li, D.Y. Zhu. Planta Med., 65, 425 (1999).
5. X.M. Du, N.Y. Sun, Y. Chen, N. Irino, Y. Shoyama. Biol. Pharm. Bull., 23, 731 (2000).
6. Jiangsu New Medical College. Dictionary of the Traditional Chinese Medicines, pp. 2283-2286, Shanghai Scientific Technologic Publishing House, Shanghai (1986).
7. W.L. Liang, R.C. Chen, Y.J. Ching, C.H. Su, L.L. Yang, K.Y. Yen. Formosan Sci., 47 (1990).
8. X.M. Du, N.Y. Sun, T. Tamura, A. Mohri, M. Sugiura, T. Yoshizawa, N. Irino, J. Hayashi, Y. Shoyama. Biol. Pharm. Bull., 24, 65 (2001).
9. T. Yoshizawa, M. Yamaura, K. Suzuki, N. Suzuki, JP 2002-14 5894 (CA: 136:401530)
10. B.L. Feringa, J.C. de Jong. Bull. Soc. Chim. Belg., 101, 627 (1992).
11. Q.H. Chen, Z. Geng, B. Huang. Tetrahedron: Asymmetry, 6, 401 (1995).
12. Y.H. Wang, Q.H. Chen. Sci. China B, 42, 121 (1999).
13. H. Huang, Q.H. Chen. Tetrahedron: Asymmetry, 10, 1295 (1999).
14. H.H. Huang, X. Zhang, Z.Y. Lin, Q.H. Chen. Chem. J. Chin. Univ., 24, 2000 (2003).
15. X.L. Zhang, H.H. Huang, Q.H. Chen. Chin. J. Org. Chem., 23, 76 (2003).
16. G.F. Huang, R.I. Hollingsworth. Tetrahedron, 54, 1355 (1998).
17. K. Mori, T. Takigawa, T. Matsuo. Tetrahedron, 35, 933 (1979).
18. A. Tanaka, K. Yamashita. Synthesis, 570 (1987).
19. R.R. Schmidt, M. Behrendt, A. Toepfer. Synlett, 694 (1990).
20. O. Mitsunobu. Synthesis, 1 (1981).
21. B.L. Feringa, B. de Lange, J.C. de Jong. J. Org. Chem., 54, 2471 (1989).
22. B.L. Feringa, B. de Lange. Tetrahedron, 44, 7213 (1988).
23. X.S. Chen, Y.L. Wu, D.H. Chen. Tetrahedron Lett., 43, 3529 (2002).
24. A. Bernardi, S. Cardani, C. Scolastico, R. Villa. Tetrahedron, 46, 1987 (1990).