Stereoselective Syntheses of (+)-Goniotriol, (+)-8-Acetylgoniotriol, (+)-Goniodiol, (+)-9-Deoxygoniopypyrone, (+)-Altholactone, and (-)-Goniofupyrone

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6619-6626

  Mukai, Chisato ^a   Hirai, Syuichi ^a   Hanaoka, Miyoji ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTONE DERIVATIVE; GONIOTHALENOL; LACTONE DERIVATIVE; NATURAL PRODUCT;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0030765653     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970725u     Document Type: Article

References (55)

1. (a) El-Zayat, A. A. E.; Ferrighi, N. R.; McKenzie, T. G.; Byrn, S. R.; Cassady, J. M.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron Lett. 1985, 26, 955.
2. (b) Alkofahi, A.; Ma, W.-W.; Mckenzie, A. T.; Byrn, S. R.; McLaughlin, J. L. J. Nat. Prod. 1989, 52, 1371.
3. (c) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; Fanwick, P. E.; McLaughlin, J. L. J. Chem. Soc., Perkin Trans. 1 1990, 1655,
4. (d) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J. L.; Fanwick, P. E. J. Nat. Prod. 1991, 54, 1034.
5. (e) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron 1991, 47, 9751.
6. (f) Fang, X.-P.; Anderson, J. E.; Qiu, X.-X.; Kozlowski, J. F.; Chang, C.-J.; McLaughlin, J. L. Tetrahedron 1993, 49, 1563.
7. (a) Tadano, K.; Ueno, Y.; Ogawa, S. Chem. Lett. 1988, 111.
8. (b) Ueno, Y.; Tadano, K.; Ogawa, S.; McLaughlin, J. L.; Alkofahi, A. Bull. Chem. Soc. Jpn. 1989, 62, 2328.
9. Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121 and references cited therein.
10. Yang, Z.-C.; Zhou, W.-C. Heterocycles 1997, 45, 367 and references cited therein.
11. Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M. Tetrahedron 1989, 45, 2627 and references cited therein.
12. Rang, S.-H.; Kim, W.-J. Tetrahedron Lett. 1989, 30, 5915.
13. (a) Honda, T.; Kametani, T.; Kanai, K.; Tatsuzaki, Y.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1990, 1733,
14. (b) Tsubuki, M.; Kanai, K.; Honda, T. J. Chem. Soc., Chem. Commun. 1992, 1640,
15. (c) Tsubuki, M.; Kanai, K.; Honda, T. Synlett 1993, 653.
16. (d) Tsubuki, M.; Kanai, K.; Honda, T. Heterocycles 1993, 35, 281.
17. Somfai, P. Tetrahedron 1994, 50, 11315.
18. (a) Surivet, J.-P.; Goré, J.; Vatèle, J. M. Tetrahedron Lett. 1996, 37, 371.
19. (b) Surivet, J.-P.; Vatèle, J.-M. Tetrahedron Lett. 1996, 37, 4373.
20. (c) Surivet, J.-P.; Goré, J.; Vatèle, J. M. Tetrahedron 1996, 52, 14877.
21. (d) Surivet, J.-P.; Volle, J.-N.; Vatèle, J.-M. Tetrahedron: Asymmetry 1996, 7, 3305.
22. (e) Surivet, J.-P.; Vatèle, J.-M. Tetrahedron Lett. 1997, 38, 819.
23. (a) Saito, S.; Harunari, T.; Shimamura, N.; Asahara, M.; Morikawa, T. Synlett 1992, 325.
24. (b) Murphy, P. J. J. Chem. Soc., Chem. Commun. 1992, 1096.
25. (c) Prakash, K. R. C.; Rao, S. P. Tetrahedron 1993, 49, 1505.
26. (d) Prakash, K. R. C.; Rao, S. P. Synlett 1993, 123.
27. (e) Ye, J.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1993, 34, 8007.
28. (a) Xu, D.; Sharpless, K. B. Tetrahedron Lett. 1994, 55, 4685.
29. (b) Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101.
30. (c) Kotora, M.; Negishi, E. Tetrahedron Lett. 1996, 37, 9041.
31. (a) Mukai, C.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1993, 34, 6081.
32. (b) Mukai, C.; Hirai, S.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547.
33. (a) Mukai, C.; Cho, W. J.; Hanaoka, M. Tetrahedron Lett. 1989, 30, 7435.
34. (b) Mukai, C.; Cho, W. J.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron 1991, 47, 3007.
35. Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1993, 55, 4346.
36. (a) Mitsunobu, O. Synthesis 1981, 1.
37. (b) Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017.
38. (c) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52.
39. (d) Barks, J. M.; Knight, D. W.; Weingarten, G. G. J. Chem. Soc., Chem. Commun. 1994, 719.
40. Vankar, Y. D.; Rao, C. T. J. Chem. Res. Synop. 1985, 232.
41. Hori, H.; Nishida, Y.; Ohrui, H. J. Org. Chem. 1989, 54, 1346.
42. (a) Felkin, I. E.; Sarda, P. Tetrahedron Lett. 1972, 725.
43. (b) Corey, E. J.; Pyne, S. G.; Su, W.-g. Tetrahedron Lett. 1983, 24, 4883.
44. (c) Honda, T.; Kametani, T.; Kanai, K.; Tatsuzaki, Y.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1990, 1733.
45. A part of the work on a synthesis of (-)-goniofupyrone was published in a preliminary communication: Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
46. (a) Hanessian, S.; Murray, P. J. J. Org. Chem. 1987, 52, 1170.
47. (b) Keck, G. E.; Romer, D. R. J. Org. Chem. 1993, 58, 6083.
48. (c) Naruse, M.; Aoyagi, S.; Kibayashi, C. J. Org. Chem. 1994, 59, 1358.
49. -1. A colorless prisms crystal, ca. 0.7 × 0.7 × 0.5 mm, was mounted on a glass fiber. All measurements were made on a Rigaku AFC5R diffractometer. The cell dimensions and intensities were refined by the least-squares method, using 25 reflections on the diffractometer with Mo Kα radiation with ω-scan mode for 2θ less than 55.1°. The structure was solved by direct method (MITHRIL method). The final cycle of full-matrix least-squares refinement was based on 3018 observed reflections. The final R value was 0.043.
50. (a) Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135.
51. (b) Kusuda, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1989, 30, 2945.
52. (c) Reed, A. D.; Hegedus, L. S. J. Org. Chem. 1995, 60, 3787.
53. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
54. Greico, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 419.
55. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.