Absolute stereochemistry of tanabalin, an insect antifeedant clerodane from Tanacetum balsamita

Chemistry Letters

Volumn , Issue 6, 1996, Pages 441-442

  Kubo, Isao ^a   Jamalamadaka, Vasu ^a   Kamikawa, Tadao ^b   Takahashi, Koichi ^b   Tabata, Kenji ^c   Kusumi, Takenori ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b KINKI UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030521851     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.441     Document Type: Article

References (21)

1. I. Kubo, in "Recent Advances in Phytochemistry," Phytochemical Potential of Tropical Plants (K. R. Downum, J. T. Romeo and H. A. Stafford, eds.), Plenum, New York (1993), Vol. 27, pp. 133-151.
2. 2.
3. I. Kubo, in "Methods in Plant Biochemistry," (K. Hostettmann and P. J. Lea, eds.), Academic Press, London (1993), Vol. 6, pp 179-193.
4. I. Kubo, Physiol. Behavior, 56, 1203 (1994).
5. 3) data for 1 (position number): δ 20.22; δ 1.11 (dq, J 3.9, 12.3), 2.05 (m) (1), δ 34.29; δ 2.17 (m), 2.40 (dm, J 18.0) (2), δ 135.51; δ 6.74 (dd, J 7.4, 2.1) (3), δ 138.63 (4), δ 45.70 (5), δ 27.82; δ 1.20 (dt, J 3.7, 13.1), 1.90 (td, J 3.0, 13.1 ) (6), δ 27.54; δ 1.45 (m), 1.60 (m) (7), δ 37.18; δ 1.62 (m) (8), δ 39.47 (9), δ 49.10; δ 1.84 (m) (10), δ 42.04; δ 1.83 (dd, J 4.5, 15.8), 2.16 (dd, J 7.7, 15.8) (11), δ 64.93; δ 5.94 (dd, J 7.7, 4.5) (12), δ 126.25 (13), δ 108.63; δ 6.40 (dd, J 1.7, 0.7) (14), δ 143.39; δ 7.36 (t, J 1.7) (15), δ 140.08; δ 7.42 (bs) (16), δ 15.66; δ 0.75 (d, J 6.5) (17), δ 17.47; δ 0.59 (s) (18), δ 77.66; δ 3.90 (dd, J 8.0, 2.0), 4.27 (d, J 8.0) (19), δ 169.98 (s) (20), δ 169.72 , 21.46; δ 2.01 (s) (Ac).
6. 12,13 However, this naming is not appropriate since this clerodane does not possess any carboxylic group.
7. w=0.045 for isotropic hydrogen atoms. C. K. Johnson, "ORTEP-II, Oak Ridge National Laboratory Report, ORNL-TM-5138", Oak Ridge, TN, USA (1976).
8. a) T. Kusumi, I. Ohtani, Y. Inouye, and H. Kakisawa, Tetrahedron Lett., 29, 4731 (1988).
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16. i) T. Kusumi, T. Hamada, M. Hara, M. O. Ishitsuka, H. Ginda, and H. Kakisawa, Tetrahedron Lett., 33, 2019 (1992).
17. 3) data for 2 (position number): δ 1.39 (1H, m) (2), 2.20 (IH, m) (2), 3.37 (1H, td, J 10.2, 4.3) (3), 3.39 (3H, s) (OMe), 2.05 (1H, d, J 10.2) (4), 1.40 (2H, m) (7), 1.72 (1H, m) (8), 2.02 (1H, dd, J 11.8, 3.3) (10), 1.61 (1H, dd, J 16.3, 2.5) (11), 1.98 (1H, dd, J 16.3, 9.0) (11), 4.85 (1H, dd, J 9.0, 2.5) (12), 6.39 (1H, bs) (14), 7.38 (1H, bs), 7.39 (1H, bs) (15 and 16), 0.77 (3H, d, J 5.0) (17), 0.57 (3H, s) (18), 4.19 (1H, dd, J 9.5, 1.0) (19), 4.16 (d, J 9.5) (19).
18. I. I. Ohtani, K. Hatta, Y. Ichikawa, and M. Isobe, Chem. Lett., 1995, 513.
19. F. Bohlmann and P. K. Mahanta, Phytochem., 18, 1067 (1979).
20. H. Y. Hsü, Y. P. Chen, and H. Kakisawa, Phytochem., 10, 2813 (1971).
21. P. R. Jefferies and T. G. Payne, Tetrahedron Lett., 4777 (1967).