Efficient synthesis of the styryllactones, (+)-goniothalamin, (+)-7-epi-goniodiol and (+)-9-deoxygoniopypyrone

Journal of Chemical Research

Volumn , Issue 1, 2004, Pages 61-63

  Liu, Zhi Yu ^a   Ji, Jian Xin ^b   Li, Bo Gang ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHENGDU INSTITUTE OF BIOLOGY   (China)

Author keywords

(+) goniothalamin; Asymmetric; Conformation; Styryllactones

Indexed keywords

7 EPIGONIODOL; 9 DEOXYGONIOPYRONE; ANTINEOPLASTIC AGENT; GONIOTHALAMIN; GONIOTHALAMUS LEIOCARPUS EXTRACT; LACTONE DERIVATIVE; NATURAL PRODUCT; STYRENE DERIVATIVE; STYRYLLACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ANNONACEAE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONFORMATION; DRUG SYNTHESIS; GONIOTHALAMUS LEIOCARPUS; ISOMER; OXIDATION; SOLUBILITY; WITTIG REACTION;

EID: 1842607115     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823404323000828     Document Type: Article

References (18)

1. a J. Rhlubucek and A.V. Robertson, Aust. J. Chem. 1967, 20, 2199;
2. (b) T.W. Sam, S.Y. Chew, S. Matsjeh, E.K. Gan, D. Razak and A.L. Mohamed, Tetrahedron Lett., 1987, 28, 2541;
3. (c) X.P. Fang, J.E. Anderson, C.J. Chang, J.L. McLaughlin and P.E. Fanwick, J. Nat. Prod., 1991, 54, 1034;
4. (d) S.H. Goh, G.C.L. Ee, C.H. Chuah and C. Wei, Aust. J. Chem. 1995, 48, 199;
5. (e) Q. Mu, W. Tang, C. Li, Y. Lu, H. Sun, H. Zheng, X. Hao, Q. Zheng, N. Wu, L. Lou and B. Xu, Heterocycles, 1999, 51, 2969.
6. (a) H.L.P. Azimahtol, E.A. Lena and N.F. Rajab, Proce. Malaysian Biochemical Society Con., 1993, 18th 177-181;
7. (b) Y.C. Wu, F.R. Chang, C.Y. Duh, S.K. Wang and T.S. Wu, Phytochemistry, 1992, 31, 2851.
8. (a) B. O'Connor and G. Just, Tetrahedron Lett., 1986, 27, 5201;
9. (b) M. Tsubuki, K. Kanai and T. Honda, Heterocycles, 1993, 35, 281;
10. (c) P.V. Ramachandran, M.V. Reddy and H.C. Brown, Tetrahedron Lett., 2000, 41, 583.
11. (a) M. Tokunaga, J. F. Larrow, F. Kakiuchi and E. N. Jacobsen, Science, 1997, 277, 936;
12. (b) D. A. Annis and E. N. Jacobsen, J. Am. Chem. Soc., 1999, 121, 4147.
13. Z.-Y. Liu, J.-X. Ji and B.-G. Li, J. Chem. Soc., Perkin Trans. 1, 2000, 3519.
14. D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4155.
15. Z.-Y. Liu, Z.-C. Chen, C.-Z. Yu, R.-F. Wang, R.-Z. Zhang, C.-S. Huang, Z. Yan, D.-R. Cao, J.-B. Sun and G. Li, Chem. Eur. J., 2002, 8, 3747.
16. H.C. Colb, M.S. Van Nieuwenhze and K.B. Sharpless, Chem. Rev., 1994, 94, 2483.
17. Z.-Y. Liu, J.-X. Ji, and B.-G. Li, A poster presentation at The Second National Symposium on Organic Chemistry, November 1-5, 2001, abstracts P328.
18. Chen also synthesised this compound using same reaction after above symposium: J. Chen, G.-Q. Lin, Z.-M. Wang, and H.-Q. Liu, Synlett, 2002, 1265.