First total synthesis and structural elucidation of (-)-goniofupyrone

Tetrahedron Letters

Volumn 37, Issue 30, 1996, Pages 5389-5392

  Mukai, Chisato ^a   Hirai, Syuichi ^a   Kim, In Jong ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; GONIOFUPYRONE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030598079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01085-4     Document Type: Article

References (26)

1. (1) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron 1991, 47, 9751-9758.
2. (2) (a) El-Zayat, A. A. E.; Ferrigni, N. R.; McCloud, T. G.; McKenzie, A. T.; Byrn, S. R.; Cassady, J. M.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron Lett. 1985, 26, 955-956.
3. (b) Gesson, J. P.; Jacquesy, J. C.; Mondon, M. Tetrahedron 1989, 45, 2627-2640.
4. (3) Ueno, Y.; Tadano, K.; Ogawa, S.; McLaughlin, J. L.; Alkofahi, A. Bull. Chem. Soc. Jpn. 1989, 62, 2328-2337.
5. (4) (a) Mukai, C.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1993, 34, 6081-6082.
6. (b) Mukai, C.; Hirai, S.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547-6560.
7. (5) Mukai, C.; Cho, W.-J.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron 1991, 47, 3007-3036.
8. (6) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 58, 4346-4359.
9. (7) The structure of (-)-7 was elucidated by its spectral evidence. Furthermore, conversion of (-)-7 into the related styryllactones, (+)-goniotriol and (+)-8-acetylgoniotriol via inversion of the allylic hydroxy group unambiguously confirmed its structure. These results combined with the detail of syntheses of (-)-goniofupyrone (2) and (+)-altholactone (3) will appear as a full paper in due course.
10. D+184.7° (EtOH)).
11. (9) For example; (a) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358-1364.
12. (b) Keck, G. E.; Romer, D. R. J. Org. Chem. 1993, 58, 6083-6089.
13. (c) Hanessian, S.; Murray, P. J. J. Org. Chem. 1987, 52, 1170-1172.
14. (10) The relative stereochemistry of two hydroxy groups at C-3 and C-4 positions was determined by X-ray crystallographic analysis of the diacetate derivative of racemic 9. This result will also be reported with the detail of this manuscript.
15. (11) Reed, A. D.; Hegedus, L. S. J. Org. Chem. 1995, 60, 3787-3794.
16. 1
17. 3-H).
18. 13C-NMR data of 2; 169.29, 137.93, 128.72, 128.46, 126.00, 86.76, 85.72, 83.65, 76.37, 65.82, 35.08.
19. 3-H).
20. 1 of goniofupyrone; 169.18, 137.90, 128.77, 128.52, 126.04, 86.67, 85.68, 83.68, 76.43, 65.85, 35.07.
21. (17) (a) Mitsunobu, O. Synthesis 1981, 1-28.
22. (b) Barks, J. M.; Knight, D. E.; Weingarten, G. G. J. Chem. Soc., Chem. Commun. 1994, 719-720.
23. (18) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666.
24. (19) Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419-420.
25. 3-H).
26. 13C-NMR data of 1; 168.88, 137.43, 128.79, 128.72, 126.25, 85.93, 84.57, 83.31, 74.11, 63.67, 34.83.