Nmr determination of the absolute configuration of an α-exo-methylene-γ-lactone

Bioscience, Biotechnology and Biochemistry

Volumn 64, Issue 7, 2000, Pages 1345-1351

  Fukui, Hiroki ^a   Fukushi, Yukiharu ^a,b   Tahara, Satoshi ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Absolute configuration; Igalan; MBCC; NOE; exo methylene lactone

Indexed keywords

LACTONE; METHYLENE LACTONE; METHYLENE-LACTONE;

ARTICLE; CHEMISTRY; CONFORMATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

LACTONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION;

EID: 0034222360     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.64.1345     Document Type: Article

References (16)

1. Yoshioka, H., Mabry, T. J., and Timmermann, B. N., ‘Sesquiterpene Lactones’, University of Tokyo Press, Tokyo (1973).
2. Fukushi, Y., Yajima, C., and Mizutani, J., Prelacinan-7-ol, a novel sesquiterpene from Rudbeckia laciniata. Tetrahedron Lett., 35, 8809-8812 (1994).
3. Fukushi, Y., Yajima, C., Mizutani, J., and Tahara, S., Tricyclic sesquiterpenes from Rudbeckia laciniata.Phytochemistry, 49, 593-600 (1998).
4. Nikonova, L. P. and Nikonov, G. K., Igalan, a new sesquiterpene lactone from Inula grandis. Khim. Prir. Soedin, 6, 508-512 (1970).
5. Bohlmann, F. and Dutta, L., A new heliangolid from Liatris platylepis. Phytochemistry, 18, 1228-1230 (1979).
6. Okunade, A. L. and Wiemer, D. F., Ant repellent sesquiterpene lactones from Eupatorium quadrangular ae. Phytochemistry, 24, 1199-1201 (1985).
7. Bohlmann, F., Jakupovic, J., Hartono, L., King, R. M., and Robinson, H., A further steiractinolide derivative from Spilanthes leiocarpa. Phytochemistry, 24, 1100-1101 (1985).
8. Jakupovic, J., Castro, V., and Bohlmann, F., Further sesquiterpene lactones from Costa Rican Eu-patorieae. Phytochemistry, 26, 451-455 (1987).
9. Jakupovic, J., Jia, Y., King, R. M., and Bohlmann, F., Rudbeckinolide, a dimeric sesquiterpene lactone from Rudbeckia laciniata. Liebigs Ann. Chem., 15, 1474-1477 (1986).
10. Zdero, C., Bohlmann, F., King, R. M., and Robinson, H., The first 12,8/?-germacrolide and other constituents from Bolivian Stevia species. Phytochemistry, 27, 2835-2843 (1988).
11. Friedrich, D. and Bohlmann, F., Total synthesis of various elemanolides. Tetrahedron, 44, 1369-1392 (1988).
12. Kato, M., Watanabe, M., Vogler, B., Awen, B. Z., Matsuda, Y., Tooyama, Y., and Yoshikoshi, A., The use of 4,4-disubstituted nopinones for natural-product synthesis. Synthesis of elemanoid sesquiterpenes. J. Org. Chem., 56, 7071-7076 (1991).
13. Ravindranath, K. R., Raghavan, R., Paknikar, S. K., Trivedi, G. K., and Bhattacharyya, S. C., Structure and stereochemistry of inunolide, dihydroinunolide and neoalantolactone. Indian J. Chem. Sect. B, 16b, 27-31 (1978).
14. Fukui, H., Fukushi, Y., and Tahara, S., NMR determination of the absolute configuration of cyclic chiral alkenes. Tetrahedron Lett., 40, 325-328 (1999).
15. Nabeta, K., Yamamoto, M., Koshino, H., Fukui, H., Fukushi, Y., and Tahara, S., Absolute configuration of kelsoene and prespatane. Biosci. Biotechnol. Biochem., 63, 1772-1776 (1999).
16. Yamakawa, K., and Tominaga, T., Japan Kokai Tokkyo Koho, 78-09758 (Jun. 28, 1978).