A novel stereocontrolled approach to eudesmanolides: Total synthesis of (±)-gallicadiol and (±)-isogallicadiol

Organic Letters

Volumn 7, Issue 14, 2005, Pages 2917-2920

  Li, Wei Dong Z ^a,b   Gao, Zhang Hua ^a  

^a LANZHOU UNIVERSITY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EUDESMANOLIDE; GALLICADIOL; LACTONE; SESQUITERPENE;

ARTEMISIA; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MEDICINAL PLANT; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ARTEMISIA; CRYSTALLOGRAPHY, X-RAY; LACTONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PLANTS, MEDICINAL; SESQUITERPENES; STEREOISOMERISM;

EID: 22244464229     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050850p     Document Type: Article

References (66)

1. For general review, see: (a) Munoz, O.; Penazola, A.; Gonzales, A. G.; Ravelo, A. G.; Bazzocchi, I. L.; Alvarenga, N. L. In Studies in Natural Product Chemistry; Atta-ür-Rahman, Ed.; Elsevier Science Publisher: Amsterdam, 1996; Vol. 18, pp 739-783.
2. For recent examples, see: (b) Goren, N. Phytochemistry 1996, 42, 747.
3. (c) Massanet, G. M.; Guerra, F. M.; Jorge, Z. D.; Astorga, C. Phytochemistry 1997, 45, 1645.
4. (d) Cho, J. Y.; Park, J.; Yoo, E. S.; Baik, K. U.; Jung, J. H.; Lee, J.; Park, M. H. Planta Med. 1998, 64, 594.
5. (e) Cantrell, C. L.; Franzblau, S. G.; Fischer, N. H. Planta Med. 2001, 67, 685.
6. For general reviews on sesquiterpene syntheses, see: (a) Heathcock, C. H. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley and Sons: New York, 1973; Vol. 2, pp 197-558.
7. (b) Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, C. T. The Total Synthesis of Natural Products; ApSimon, J., Ed.; John Wiley and Sons: New York, 1983; Vol. 5.
8. (c) Spivey, A. C.; Weston, M.; Woodhead, S. Chem. Soc. Rev. 2002, 31, 43.
9. For examples, see: (a) Ando, M.; Akahane, A.; Takase, K. Bull. Chem. Soc. Jpn. 1978, 51, 283.
10. (b) Garcia-Granados, A.; Martinez, A.; Parra, A.; Rivas, F.; Onorato, M. E.; Arias, J. M. Tetrahedron 1993, 49, 1091.
11. (c) Miyashita, M.; Suzuki, T.; Yoshikoshi, A. Chem. Lett. 1987, 2387.
12. (d) Bargues, V.; Blay, G.; Garcia, B.; Garcia, C. L.; Pedro, J. R. Tetrahedron 1995, 51, 5609.
13. For examples, see: (a) Abe, Y.; Harukawa, T.; Ishikawa, H.; Miki, T.; Sumi, M.; Toga, T. J. Am. Chem. Soc. 1956, 78, 1422.
14. (b) Van Hijfte, L.; Vandewalle, M. Tetrahedron 1984, 40, 4371.
15. (c) Macias, F. A.; Aguilar, J. M.; Molinillo, J. M. G.; Rodriguez-Luis, F.; Collado, I. G.; Massanet, G. M.; Fronczek, F. R. Tetrahedron 2000, 56, 3409.
16. For previous studies from this laboratory, see: (a) Zhou, G.; Gao, X.-L.; Li, W.-D. Z.; Li, Y.-L. Tetrahedron Lett. 2001, 42, 3101.
17. (b) Li, W.-D. Z.; Zhou, G.; Gao, X.-L.; Li, Y.-L. Tetrahedron Lett. 2001, 42, 4649.
18. (c) Zhang, Z.; Li, W.-D. Z.; Li, Y.-L. Org. Lett. 2001, 3, 2555.
19. Gonzalez, A. G.; Galindo, A.; Mansilla, H.; Kesternich, V. H.; Palenzuela, J. A.; Lopez, M. Tetrahedron 1988, 44, 6750.
20. (a) Gonzalez, A. G.; Galindo, A.; Hansilla, H.; Kesternich, V. H.; Palenzuela, J. A.; Rodriguez, M. L. J. Nat. Prod. 1990, 53, 462.
21. (b) Trendafilova, A. B.; Todorova, M. N.; Gussev, C. V. Photochemistry 1996, 42, 469.
22. For general reviews, see: (a) Cane, D. E. Chem. Rev. 1990, 90, 1089.
23. (b) Banthorpe, D. V. In Natural Products: Their Chemistry and Biological Significance; Mann, J., Davidson, R. S., Hobbs, J. B., Banthorpe, D. V., Harborne, J. B., Eds.; Longman Scientific & Technical: Essex, U.K., 1994; pp 316-327.
24. (c) Marco, J. A.; Sanz-Cervera, J. F.; Garcia-Lliso, V.; Domingo, L. R.; Carda, M.; Rodriguez, S.; Lopez-Ortiz, F.; Lex, J. Liebigs Ann. 1995, 1837.
25. (d) Minnaard, A. J.; Stork, G. A.; Wijnberg, J. B. P. A.; De Groot, A. J. Org. Chem. 1997, 62, 2344.
26. (e) Steele, C. L.; Crock, J.; Bohlmann, J.; Croteau, R. J. Biol. Chem. 1998, 273, 2078.
27. (f) Seemann, M.; Zhai, G.; Umezawa, K.; Cane, D. E. J. Am. Chem. Soc. 1999, 121, 591.
28. (a) Rodrígues, A. A. S.; García, M.; Rabi, J. A. Phytochemistry 1978, 17, 953.
29. (b) El-Feraly, F. S.; Benigni, D. A.; McPhail, A. T. J. Chem. Soc., Perkin Trans. 1 1983, 355.
30. (c) Barrero, A. F.; Sánchez, J. F.; Barrón, A.; Ramírez, A. Phytochemistry 1992, 31, 332.
31. Ogura, M.; Cordell, G. A.; Farnsworth, N. R. Phytochemistry 1978, 17, 957.
32. Gonzalez, A. G.; Galindo, A.; Mansilla, H.; Gutierrez, A. J. Chem. Soc., Perkin Trans. 1 1982, 881.
33. For other cationic cyclization approaches to decaline ring system, see: Cooper, J. L.; Harding, K. E. Tetrahedron Lett. 1977, 18, 3321 and references therein.
34. Other substituents bearing a heteroatom, such as S, Si, or Cl, would be alternative choices.
35. (a) Magnus, P.; Roy, G. Organometallics 1982, 1, 553.
36. (b) For an applicable example in synthesis, see: Kende, A. S.; Blacklock, T. J. Tetrahedron Lett. 1980, 21, 3119.
37. See Supporting Information-1 for experimental details.
38. Corey, E. J.; Tius, M. A. Tetrahedron Lett. 1980, 21, 3535.
39. (a) Ohira, S. Synth. Commun. 1989, 19, 561.
40. (b) Surprenant, S.; Chan, W. Y.; Berthelette, C. Org. Lett. 2003, 5, 4851.
41. Blay, G.; Cardona, L.; Garcia, B.; Garcia, C. L.; Pedro, J. R. Tetrahedron Lett. 1994, 35, 931.
42. For relevant examples of this type of 1,3-shift, see: (a) Finnerty, J.; Andraos, J.; Yamamoto, Y.; Wong, M. W.; Wentrup, C. J. Am. Chem. Soc. 1998, 120, 1701.
43. (b) Fulloon, B. E.; Wentrup, C. J. Org. Chem. 1996, 61, 1363. Further study of this mechanistic pathway is underway.
44. Further studies are ongoing to restrain this seemingly inevitable migration by attaching an electron-donating group (i.e., trimethylsilyl) at the allylic terminal of the homoprenyl chain in 4b.
45. (a) Marshall, J. A.; Wuts, P. G. M. J. Am. Chem. Soc. 1978, 100, 1627.
46. (b) Schwartz, M. A.; Crowell, J. D.; Musser, J. H. J. Am. Chem. Soc. 1972, 94, 4361.
47. 4, FW 294.38, monoclinic, space group C2/c, a = 16.846(8) Å, b = 18.842(8) Å, c = 11.732-
48. 2 (all data) = 0.1048. See Supporting Information-1 for more details.
49. (23) Stereostructures were characterized spectroscopically.
50. Obviously, hydroboration of the terminal olefin of 15 took place first and was followed by intramolecular face-specific hydride transfer from boron to the C-6 carbonyl, leading to 6α-hydroxy.
51. For leading references, see: (a) Balogh, V.; Fetizon, M.; Golfier, M. J. Org. Chem. 1971, 36, 1339.
52. (b) Fetizon, M.; Golfier, M.; Louis, J.-M. Tetrahedron 1975, 31, 171.
53. For alternative hydroboration-oxidative γ-lactonization sequences, see: (c) Jefford, C. W.; Wang, Y. J. Chem. Soc., Chem. Commun. 1988, 634.
54. (d) Chavan, S. P.; Zubaidha, P. K.; Dhondge, V. D. Tetrahedron 1993, 49, 6429.
55. (26) Both relactonization and acid-mediated epoxy ring-opening of the resulting deacetylation intermediate took place at this stage.
56. Authentic sample of 6 is not available for direct comparison.
57. 3N), which were fully characterized spectroscopically; see Supporting Information-1 for details.
58. The corresponding ring-opening product of γ-lactone, dihydroxy methyl ester, was obtained in ca. 20% yield.
59. A minor product (ca. 10%) was identified as the C-1 O-silylated gallicadiol (6).
60. (31) Corresponding to C-1 acetates of 14 and 14a, respectively.
61. 5c See: Guan, Y.-K.; Li, Y.-L. Chirality 2005, 17, 113.
62. For examples, see: (a) Heathcock, C. H.; Ratcliffe, R.; Van, J. J. Org. Chem. 1972, 37, 1796.
63. (b) Minnaard, A. J.; Wijnberg, J. B. P. A.; De Groot, A. Tetrahedron 1994, 50, 4755.
64. For examples, see: (a) Xu, F.; Morikawa, T.; Matsuda, H.; Ninomiya, K.; Yoshikawa, M. J. Nat. Prod. 2004, 67, 569.
65. (b) Kawaguchi, Y.; Ochi, T.; Takaishi, Y.; Kawazoe, K.; Lee, K.-H. J. Nat. Prod. 2004, 67, 1893.
66. (c) Sun, Z.; Chen, B.; Zhang, S.; Hu, C. J. Nat. Prod. 2004, 67, 1975.