Mersiphyllines A and B from Kopsia. Determination of relative configuration at a quaternary center via formation of an alkaloid-borane complex

Tetrahedron

Volumn 65, Issue 34, 2009, Pages 6873-6876

  Low, Yun Yee ^a   Subramaniam, G ^b   Lim, Kuan Hon ^a   Wong, Richard C S ^a   Robinson, Ward T ^a   Kam, Toh Seok ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b SCHOOL OF ENGINEERING   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; BORANE DERIVATIVE; CARBOXYLIC ACID; MERSIPHYLLINE A; MERSIPHYLLINE B; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG ISOLATION; DRUG STRUCTURE; KOPSIA SINGAPURENSIS; MEDICINAL PLANT; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY DIFFRACTION;

KOPSIA;

EID: 67650529060     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.079     Document Type: Article

References (18)

1. Subramaniam G., Choo Y.M., Hiraku O., Komiyama K., and Kam T.S. Tetrahedron 64 (2008) 1397
2. Kam T.S., Subramaniam G., and Lim T.M. Tetrahedron Lett. 42 (2001) 5977
3. Kam T.S., and Lim K.H. In: Cordell G.A. (Ed). The Alkaloids: Chemistry and Biology Vol. 66 (2008), Academic, The Netherlands 1
4. Kam T.S., Subramaniam G., Lim K.H., and Choo Y.M. Tetrahedron Lett. 45 (2004) 5995
5. Kam T.S., and Subramaniam G. Tetrahedron Lett. 45 (2004) 3521
6. Subramaniam G., and Kam T.S. Tetrahedron Lett. 48 (2007) 6677
7. Subramaniam G., Hiraku O., Hayashi M., Koyano T., Komiyama K., and Kam T.S. J. Nat. Prod. 71 (2008) 53
8. Subramaniam G., Kam T.S., and Ng S.W. Acta Crystallogr. E59 (2003) o555
9. Hashimoto N., Aoyama T., and Shioiri T. Chem. Pharm. Bull. 29 (1981) 1475
10. Rosen W.E. Tetrahedron Lett. (1961) 481
11. Wenkert E., Guo M., Pestchanker M.J., Shi Y.J., and Vankar Y.D. J. Org. Chem. 54 (1989) 1166
12. Miller N.E. Inorg. Chem. 13 (1974) 1459
13. Corey E.J., Bakshi R.K., and Shibata S. J. Am. Chem. Soc. 109 (1987) 5551
14. Leach J.B., Ungermann C.B., and Onak T.P. J. Magn. Reson. 6 (1972) 74
15. Nung M.Y., Chwang S.P., Brown H.C., Krishnamurthy S., and Stocky T.P. J. Org. Chem. 38 (1973) 2876
16. Brown H.C., and Stocky T.P. J. Am. Chem. Soc. 99 (1977) 8218
17. The X-ray crystal structure showed that 1 exists in the crystal lattice in its zwitterionic form.
18. Wang A.H.J., and Paul I.C. Acta Crystallogr. B33 (1977) 2977