Facile and enantiospecific syntheses of goniotriol analogues

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 2140-2144

  Shing, Tony K M ^a   Tai, Vincent W F ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,8 TRIDEOXY GLUCO OCT 2 ENONO DELTA LACTONE; LACTONE; UNCLASSIFIED DRUG; XYLO HEPT 2 ENONO DELTA LACTONE;

CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROLYSIS; ISOLATION AND PURIFICATION; NOTE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; SOLUBILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033583168     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982159o     Document Type: Note

References (61)

1. (a) Wu, Y. C.; Duh, C. Y.; Chang, F. R.; Chang, G. Y.; Wang, S. K.; Chang, J. J.; McPhail, D. R.; McPhail, A. T.; Lee, K. H. J. Nat. Prod. 1991, 54, 1077.
2. (b) Talapatra, S. K.; Basu, D.; Deb, T.; Goswami, S.; Talapatra, B. Indian J. Chem. 1985, 24B, 29.
3. (c) Sam, T. W.; Chew, S.-Y.; Matsjeh, S.; Gan, E. K.; Razak, D.; Mohamed, A. L. Tetrahedron Lett. 1987, 28, 2541.
4. (d) Geran, R. I.; Greenberg, N. H.; MacDonald, M. M.; Schumacher, A. M.; Abbott, B. J. Cancer Chemother. Res. 1972, 3, 1.
5. Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; Fanwick, P. E.; McLaughlin J. L. J. Chem. Soc., Perkin Trans. 1 1990, 1655.
6. Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin J. L.; Fanwick, P. E. J. Nat. Prod. 1991, 54, 1034.
7. Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; McLaughlin J. L. Tetrahedron 1991, 47, 9751.
8. 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.
9. Alkofahi, A.; Ma, W.-W.; Mckenzie, A. T.; Byrn, S. R.; McLaughlin, J. L. J. Nat. Prod. 1989, 52, 1371.
10. Examples of our earlier efforts: (a) Synthesis of (+)-altholactone and stereoisomers from D-gulonolactone, see: Gillhouley, J. G.; Shing, T. K. M. J. Chem. Soc., Chem. Commun. 1988, 976. Tetrahedron 1994, 50, 8685.
11. Examples of our earlier efforts: (a) Synthesis of (+)-altholactone and stereoisomers from D-gulonolactone, see: Gillhouley, J. G.; Shing, T. K. M. J. Chem. Soc., Chem. Commun. 1988, 976. Tetrahedron 1994, 50, 8685.
12. (b) Synthesis of the (6R,7S)-diastereoisomer of asperlin from D-glucose, see: Shing, T. K. M.; Aloui, M. J. Chem. Soc., Chem. Commun. 1988, 1525. Can. J. Chem. 1990, 68, 1035.
13. (b) Synthesis of the (6R,7S)-diastereoisomer of asperlin from D-glucose, see: Shing, T. K. M.; Aloui, M. J. Chem. Soc., Chem. Commun. 1988, 1525. Can. J. Chem. 1990, 68, 1035.
14. (a) Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. J. Org. Chem. 1995, 60, 3121.
15. (b) Shing, T. K. M.; Tai, V. W.-F.; Tsui, H.-C. J. Chem. Soc., Chem. Commun. 1994, 1293.
16. (c) Shing, T. K. M.; Tsui, H.-C. Tetrahedron: Asymmetry 1994, 5, 1269.
17. (c) Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron Lett. 1993, 34, 691.
18. (d) J. Chem. Soc., Chem. Commun. 1992, 810.
19. (e) Shing, T. K. M.; Tsui, H.-C. J. Chem. Soc., Chem. Commun. 1992, 432.
20. (f) Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron 1992, 48, 8659.
21. (g) Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans 1 1992, 887.
22. (h) Shing, T. K. M.; Zhou, Z.-H. Tetrahedron Lett. 1992, 33, 3333.
23. (i) Shing, T. K. M.; Tsui, H.-C.; Zhou, Z.-H. Tetrahedron 1992, 48, 8659.
24. (j) Shing, T. K. M.; Zhou, Z.-H.; Mak, T. C. W. J. Chem. Soc., Perkin Trans 1 1992, 1907.
25. Syntheses of ent-(-)-goniofufurone and ent-(-)-7-epi-goniofufurone: (a) Gracza, T.; Jäger, V. Synlett. 1992, 191.
26. (b) Prakash, K. R. C.; Rao, S. P. Synlett 1093, 123.
27. (c) Gracza, T.; Jäger, V. Synthesis 1994, 1359.
28. Synthesis of (+)-goniofufurone: (d) Murphy, P. J. J. Chem. Soc., Chem. Commun. 1992, 1096.
29. (e) Murphy, P. J.; Dennison S. T. Tetrahedron 1993, 49, 6695.
30. (f) Prakash, K. R. C.; Rao, S. P. Tetrahedron 1993, 49, 1505.
31. (g) Tsubuki, M.; Kanai, K.; Honda, T. Synlett 1993, 653.
32. (h) Mukai, C.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1993, 34, 6081.
33. (i) Ye, J.; Bhatt, R. K.; Falck, J. R. Tetrahedron Lett. 1993, 34, 8007.
34. (j) Yang, Z.-C.; Zhou, W.-S. Tetrahedron 1995, 51, 1429.
35. (k) Mukai, C.; Hirai, S.; Kim, I. J.; Kido, M.; Hanaoka, M. Tetrahedron 1996, 52, 6547.
36. (l) Surivet, J.-P.; Vatele, J.-M. Tetrahedron Lett. 1996, 37, 4373.
37. (m) Yi, X. H.; Meng Y.; Li, C. J. Chem. Commun. 1998, 449.
38. Synthesis of (+)-7-epi-goniofufurone: (n) Yang, Z.-C.; Zhou, W.-S. J. Chem. Soc., Perkin Trans 1 1994, 3231.
39. (o) Surivet J.-P.; Vatele J.-M. Tetrahedron Lett. 1997, 38, 819.
40. Syntheses of (+)-goniobutenolide A and (-)-goniobutenolide B: (a) Xu, D.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 4658.
41. (b) Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101.
42. (c) Negishi E.; Kotora M. Tetrahedron 1997, 53, 6707.
43. (d) see ref 9k.
44. Synthesis of (+)-goniopypyrone: (a) Zhou, W.-S.; Yang, Z.-C. Tetrahedron Lett. 1993, 34, 7075.
45. (b) Yang Z.-C., Zhou W. S. Chin. J. Chem. 1996, 14, 152.
46. (c) see ref 9g.
47. Synthesis of (+)-altholactone: (a) Gesson, J. P.; Jacquesy, J. C.; Mondon, M. Tetrahedron 1989, 45, 2627.
48. (b) Ueno, Y.; Tadano, K.; Ogawa, S.; McLaughlin, J. L.; Alkofahi, A. Bull. Chem. Soc. Jpn. 1989, 62, 2328.
49. (c) Kang, S. H.; Kim W. J.Tetrahedron Lett. 1989, 30, 5915.
50. (d) Somfai, P.; Tetrahedron 1994, 50, 11315.
51. (e) Mukai, C.; Hirai, S.; Hanaoka, M. J. Org. Chem. 1997, 62, 6619.
52. (f) see ref 9g.
53. Syntheses of (+)-goniotriol and (+)-7-acetylgoniotriol: (a) Yang Z. C.; Zhou W. S. Chin. Chem. Lett. 1996, 7, 319.
54. (b) see ref 9g, ref 9j, and ref 12e.
55. For a review, see: Shing, T. K. M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 703.
56. (a) Valverde, S.; Lomas, M. M.; Herradon B.; Ochoa, S. G. Tetrahedron 1987, 43, 1895.
57. (b) Tronchet, J. M. J.; Gentile, B. Helv. Chim. Acta 1979, 62, 2091.
58. (c) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
59. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Organic Compounds, 4th ed., John Wiley & Sons: New York, 1981; Chapters 4 and 5.
60. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. Review, see Rychnovsky, S. D.; Rogers, B.; Richardson, T. I. Ace. Chem. Res. 1998, 31, 9.
61. Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. Review, see Rychnovsky, S. D.; Rogers, B.; Richardson, T. I. Ace. Chem. Res. 1998, 31, 9.