Xyloccensins Q-V, six new 8,9,30-phragmalin ortho ester antifeedants from the Chinese mangrove Xylocarpus granatum

Tetrahedron

Volumn 61, Issue 35, 2005, Pages 8382-8389

  Wu, Jun ^a   Xiao, Qiang ^b   Zhang, Si ^a   Li, Xiang ^a   Xiao, Zhihui ^a   Ding, Haixin ^b   Li, Qingxin ^a  

^a SOUTH CHINA SEA INSTITUTE OF OCEANOLOGY   (China)

^b JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

8,9,30 Phragmalin ortho ester; Absolute stereochemistry; Antifeedant activity; Xylocarpus granatum

Indexed keywords

PLANT EXTRACT; UNCLASSIFIED DRUG; XYLOCCENSIN O; XYLOCCENSIN P; XYLOCCENSIN Q; XYLOCCENSIN R; XYLOCCENSIN S; XYLOCCENSIN T; XYLOCCENSIN U; XYLOCCENSIN V;

ARTICLE; BARK; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; DRUG ISOLATION; ENANTIOMER; LARVA; MANGROVE; MEDICINAL PLANT; PRIORITY JOURNAL; SPECTROSCOPY; STEREOCHEMISTRY; TREE TRUNK; XYLOCARPUS GRANATUM;

MYTHIMNA SEPARATA; XYLOCARPUS GRANATUM;

EID: 23044479404     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.06.099     Document Type: Article

References (20)

1. D.E. Champagne, O. Koul, M.B. Isman, G.G.E. Scudder, and G.H.N. Towers Phytochemistry 31 1992 377 394
2. J.H. Butterworth, and E.D. Morgan Chem. Commun. 1968 23 24
3. D.A.H. Taylor Tetrahedron 43 1987 2779 2787
4. M.S. Rajab, J.K. Rugutt, F.R. Fronczek, and N.H. Fischer J. Nat. Prod. 60 1997 822 825
5. I. Kubo, S.P. Tanis, Y.W. Lee, I. Miura, K. Nakanishi, and A. Chapya Heterocycles 5 1976 485 498
6. A.S. Ng, and A.G. Fallis Can. J. Chem. 57 1979 3088 3089
7. I. Kubo, I. Miura, and K. Nakanishi J. Am. Chem. Soc. 98 1976 6704 6705
8. K.A. Alvi, P. Crews, B. Aalbersberg, R. Prasad, J. Simpson, and R.T. Weavers Tetrahedron 47 1991 8943 8948
9. D.A. Mulholland, B. Parel, and P.H. Coombes Curr. Org. Chem. 4 2000 1011 1054
10. U. Kokpol, W. Chavasiri, S. Tip-pyang, G. Veerachato, and F.L. Zhao Phytochemistry 41 1995 903 905
11. J. Wu, S. Zhang, Q. Xiao, Q.X. Li, J.S. Huang, Z.H. Xiao, and L.J. Long Z. Naturforschung 58b 2003 1216 1219
12. J. Wu, S. Zhang, Q. Xiao, Q.X. Li, J.S. Huang, L.J. Long, and L.M. Huang Tetrahedron Lett. 45 2004 591 593
13. J. Wu, Q. Xiao, J.S. Huang, Z.H. Xiao, S.H. Qi, Q.X. Li, and S. Zhang Org. Lett. 6 2004 1841 1844
14. I. Ohtani, T. Kusumi, Y. Kashman, and H. Kakisawa J. Am. Chem. Soc. 113 1991 4092 4096
15. T. Kusumi, T. Fukushima, I. Ohtani, and H. Kakisawa Tetrahedron Lett. 32 1991 2929 2942
16. B.N. Su, E.J. Park, Z.H. Mbwambo, B.D. Santarsiero, A.D. Mesecar, H.H.S. Fong, J.M. Pezzuto, and A.D. Kinghorn J. Nat. Prod. 65 2002 1278 1282
17. K. Takada, T. Uehara, Y. Nakao, S. Matsunaga, R.W.M.V. Soest, and N. Fusetani J. Am. Chem. Soc. 126 2004 187 193
18. S.A.M. Abdelgaleil, H. Okamura, T. Iwagawa, A. Sato, I. Miyahara, M. Doe, and M. Makatani Tetrahedron 57 2001 119 126
19. Detected in the mixture of MTPACl [(R)- or (S)-] and DMAP. The aromatic proton signals of the MTPA fragment of 10a and 10b are overlapped with that of the reacting reagents.
20. ND: not detected for the split and low intensity caused by C-F coupling.