Absolute stereocmemistry of halichlorine; a potent inhibitor of VCAM-1 induction

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 861-862

  Arimoto, Hirokazu ^a   Hayakawa, Ichiro ^a   Kuramoto, Makoto ^b   Uemura, Daisuke ^c  

^a SHIZUOKA UNIVERSITY   (Japan)

^b EHIME UNIVERSITY   (Japan)

^c NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

HALICHLORINE; NATURAL PRODUCT; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1;

ARTICLE; CONTROLLED STUDY; DEGRADATION; DRUG SYNTHESIS; JAPAN; NONHUMAN; PROTEIN EXPRESSION; STEREOCHEMISTRY;

EID: 0032546135     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10714-6     Document Type: Article

References (8)

1. 1. Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867-3870.
2. 3OD) δ 0.99(3H, d, J= 6.8 Hz), 1.20(1H, m), 1.25(1H, m), 1.25(1H, m), 1.40(1H, m), 1.40(1H, m), 1.40(1H, dd, J=12.9, 3.9 Hz), 1.45(1H, m), 1.53(1H, m), 1.73(1H, m), 1.77(1H, m), 2.02(1H, m, J=19.0 Hz), 2.11(1H, m), 2.24(1H, m), 2.34(1H, m), 2.37(1H, m), 2.93(1H, dddd, J= 15.7, 3.9, 3.0, 1.2 Hz), 3.47(1H, br.d, J= 15.7 Hz), 3.72(3H, s), 3.73(2H, m), 4.97(1H, J= 7.8, 6.3, 0.9 Hz), 5.38(1H, ddd, J= 15.6, 6.3, 1.1 Hz), 5.63(1H, dd, 7.8, 0.8 Hz), 5.94(1H, ddd, J= 15.6, 7.7, 0.9 Hz), 6.87(1H, br.s):
3. 3) δ 2.04(3H, s), 2.07(3H, s), 2.07(3H, s), 2.67(2H, t, J=6.3 Hz), 4.13 (1H, dd, J=6.7, 11.8 Hz), 4.2 (3H, complex), 5.57 (1H, J=7.6 Hz)
4. 3. Takano, S.; Yoshimitsu, T.; Ogasawara, K. Synlett 1994, 119-120. (equation presented)
5. 4. Yadav, J. S.; Chander, M. C.; Joshi, B.V. Tetrahedron Lett. 1988, 29, 2737-2740.
6. 3)
7. 7 another marine natural product isolated in these laboratories. Halichlorine and pinnaic acid share same skeltone, and the stereochemistry of 14 was not fully established. Although we proposed different relative stereochemistries at the C14 for each natural product, the results were not conclusive. A synthetic effort to clarify this point is currently underway.
8. 7. Chou, T.; Kuramoto, M.; Ohtani, Y.; Shikano, M.; Yazawa, K.; Uemura, D. Tetrahedron Lett. 1996, 37, 3871-3874.