Synthetic Studies on Polypropionate-Derived 4-Pyrone-Containing Marine Natural Products

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 9, 1997, Pages 2025-2037

  Yamamura, Shosuke ^a,b,c   Nishiyama, Shigeru ^a  

^a KEIO UNIVERSITY   (Japan)

^b Naoya Nunversity ^*

^c MEIJO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001559610     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.2025     Document Type: Article

References (78)

1. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
2. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
3. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
4. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
5. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
6. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
7. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
8. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
9. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
10. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
11. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
12. Review: D. J. Faulkner, Nat. Prod. Rep., 1, 251 (1984); Nat. Prod. Rep., 1, 551; Nat. Prod. Rep., 3, 1 (1986); Nat. Prod. Rep., 4, 539 (1987); Nat. Prod. Rep., 5, 613 (1988); Nat. Prod. Rep., 7, 269 (1990); Nat. Prod. Rep., 8, 97 (1991); Nat. Prod. Rep., 9, 323 (1992); Nat. Prod. Rep., 10, 497 (1993); Nat. Prod. Rep., 11, 355 (1994); Nat. Prod. Rep., 12, 223 (1995); Nat. Prod. Rep., 13, 75 (1996).
13. J. R. Pawlik, Chem. Rev., 93, 1911 (1993).
14. a) Isolation from Siphonaria zelandica, S. atra, S. normaris, and S. laciniosa: J. E. Hochlowski, J. C. Coll, D. J. Faulkner, J. E. Biskupiak, C. M. Ireland, Z. Qi-tai, H. Cun-heng, and J. Clardy, J. Am. Chem. Soc., 106, 6748 (1984);
15. b) Biosynthesis and X-ray analysis: M. J. Garson, D. D. Jones, C. J. Small, J. Liang, and J. Clardy, Tetrahedron Lett., 35, 6921 (1994);
16. c) Absolute configuration: I. Paterson and A. S. Franklin, Tetrahedron Lett., 35, 6925 (1994);
17. d) Configurational model: M. J. Garson, J. M. Goodman, and I. Paterson, Tetrahedron Lett., 35, 6929 (1994).
18. Isolation from Siphonaria baconi: D. C. Manker, D. J. Faulkner, T. J. Stout, and J. Clardy, J. Org. Chem., 54, 5371 (1989).
19. a) Isolation from Siphonaria maura: D. C. Manker and D. J. Faulkner, J. Org. Chem., 54, 5374 (1989);
20. b)Synthesis: H. Arimoto, R. Yokoyama, and Y. Okumura, Tetrahedron Lett., 37, 4749 (1996); H. Arimoto, R. Yokoyama, K. Nakamura, Y. Okumura, and D. Uemura, Tetrahedron, 52, 13901 (1996).
21. b)Synthesis: H. Arimoto, R. Yokoyama, and Y. Okumura, Tetrahedron Lett., 37, 4749 (1996); H. Arimoto, R. Yokoyama, K. Nakamura, Y. Okumura, and D. Uemura, Tetrahedron, 52, 13901 (1996).
22. Isolation from Placida dendritica: R. R. Vardaro, V. Di Marzo, and G. Cimino, Tetrahedron Lett., 33, 2875 (1992).
23. Isolation from Siphonaria maura: D. C. Manker, D. J. Faulkner, X. Chang-fu, and J. Clardy, J. Org. Chem., 51, 814 (1986).
24. Isolation from Tridachia crispata: M. B. Ksebati and F. J. Schmilz, J. Org. Chem., 50, 5637 (1985).
25. Isolation from Tridachiella diomedea: C. M. Ireland and D. J. Faulkner, Tetrahedron, 37, Suppl. 1, 233 (1981).
26. Isolation from Tridachia crispata see: Ref. 9.
27. Isolation from Dolabella auricularia: K. Suenaga, H. Kigoshi, and K. Yamada, Tetrahedron Lett., 37, 5151 (1996).
28. Isolation from Cyerce cristallina: R. R. Vardaro, V. Di Marzo, A. Crispino, and G. Cimino, Tetrahedron, 47, 5569 (1991); Related compounds: R. R. Vardaro, V. Di Marzo, A. Marin, and G. Cimino, Tetrahedron, 48, 9561 (1992).
29. Isolation from Cyerce cristallina: R. R. Vardaro, V. Di Marzo, A. Crispino, and G. Cimino, Tetrahedron, 47, 5569 (1991); Related compounds: R. R. Vardaro, V. Di Marzo, A. Marin, and G. Cimino, Tetrahedron, 48, 9561 (1992).
30. Isolation from Elysia chlorotica: R. D. Dawe and J. L. C. Wright, Tetrahedron Lett., 27, 2559 (1986). This compound has the same plane structure as those of tridachiapyrone A and isotridachiapyrone A (Ref. 8).
31. Isolation from Siphonaria zelandica: J. T. Blanchfield, T. Joanne, D. J. Brecknell, J. Douglas, I. M. Brereton, M. J. Garson, and D. D. Jones, Aust. J. Chem., 47, 2255 (1994).
32. Isolation from Onchidium verruculalum: C. M. Ireland, J. E. Biskupiak, G. J. Hite, M. Rapposch, P. J. Scheuer, and J. R. Ruble, J. Org. Chem., 49, 559 (1984).
33. Isolation from Peronia peronii: J. E. Biskupiak and C. M. Ireland, Tetrahedron Lett., 26, 4307 (1985).
34. Isolation from Onchidium sp.: J. Rodrguez, R. Riguera, and C. Debitus, Tetrahedron Lett., 33, 1089 (1992); J. Org. Chem., 57, 4624 (1992).
35. Isolation from Onchidium sp.: J. Rodrguez, R. Riguera, and C. Debitus, Tetrahedron Lett., 33, 1089 (1992); J. Org. Chem., 57, 4624 (1992).
36. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
37. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
38. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
39. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
40. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
41. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
42. 4: R. J. Light and C. R. Hauser, J. Org. Chem., 25, 538 (1960); g) 45% HBr: W. I. O'sullivan and C. R. Hauser, J. Org. Chem., 25, 1110 (1960).
43. Recently, this methodology was published by employing a 2-pyrone derivative: X. Shi, W. S. Leal, Z. Liu, E. Schrader, and J. Meinwald, Tetrahedron Lett., 36, 71 (1995).
44. H. Arimoto, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 31, 5619 (1990).
45. H. Arimoto, S. Ohba, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 35, 4581 (1994). This result revised the structures of products by the tandem aldol-Swern oxidation process proposed as a method for triketide synthesis, see; N. E. Pratt, Y -B. Zhao, S. Hitchcock, and K. F. Albizati, SYNLETT, 1991, 361.
46. H. Arimoto, S. Ohba, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 35, 4581 (1994). This result revised the structures of products by the tandem aldol-Swern oxidation process proposed as a method for triketide synthesis, see; N. E. Pratt, Y -B. Zhao, S. Hitchcock, and K. F. Albizati, SYNLETT, 1991, 361.
47. H. Arimoto, J. -F. Cheng, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 34, 5781 (1993)
48. The difference of the magnitudes between the both optical rotations may be due to an insufficient sample amount causing an experimental error.
49. H. Arimoto, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 31, 5491 (1990).
50. D. Seebach, H. -F. Chow, R. F. W. Jackson, K. Lawson, M. A. Sutter, S. Thnisrivongs, and J. Zimmermann, J. Am. Chem. Soc., 107, 5292 (1985).
51. K. Mori and H. Iwasawa, Tetrahedron, 36, 87 (1980).
52. R. F. W. Jackson, M. A. Sutter, and D. Seebach, Liebigs Ann. Chem., 1985, 2313.
53. B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal, J. M. Balkovec, J. J. Baldwin, M. E. Christy, G. S. Ponticello, S. L. Varga, and J. P. Springer, J. Org. Chem., 51, 2370 (1986); B. M. Trost and D. P. Curran, Tetrahedron Lett., 22, 4929 (1981).
54. B. M. Trost, J. L. Belletire, S. Godleski, P. G. McDougal, J. M. Balkovec, J. J. Baldwin, M. E. Christy, G. S. Ponticello, S. L. Varga, and J. P. Springer, J. Org. Chem., 51, 2370 (1986); B. M. Trost and D. P. Curran, Tetrahedron Lett., 22, 4929 (1981).
55. The 10R configuration of 5 was deduced by the stereochemical relationship with 3 as follows. Riguera et al. recognized 5 had the same relative stereochemistry at the C3, 4, 13, 14, 15, and 16 positions as that of 3(3R*, 4R*, 10R*, 13R*, 14S*, 15S*, 16S*). Since the optical rotations indicated a diastereomer relationship between 3 and 5, the configuration at the C10 position "must be 10R in 5".
56. H. Arimoto, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 35, 9581 (1994).
57. H. Arimoto, Y. Okumura, S. Nishiyama, and S. Yamamura, Tetrahedron Lett., 36, 5357 (1995).
58. K. Takai, K. Kimura, T. Kuroda, T. Hiyama, and H. Nozaki, Tetrahedron Lett., 24, 5281 (1983); H. Jin, J. Uenishi, W. J. Christ, and Y. Kishi, J. Am. Chem. Soc., 108, 5644 (1986); Y. Kishi, Pure Appl. Chem., 64, 343 (1992).
59. K. Takai, K. Kimura, T. Kuroda, T. Hiyama, and H. Nozaki, Tetrahedron Lett., 24, 5281 (1983); H. Jin, J. Uenishi, W. J. Christ, and Y. Kishi, J. Am. Chem. Soc., 108, 5644 (1986); Y. Kishi, Pure Appl. Chem., 64, 343 (1992).
60. K. Takai, K. Kimura, T. Kuroda, T. Hiyama, and H. Nozaki, Tetrahedron Lett., 24, 5281 (1983); H. Jin, J. Uenishi, W. J. Christ, and Y. Kishi, J. Am. Chem. Soc., 108, 5644 (1986); Y. Kishi, Pure Appl. Chem., 64, 343 (1992).
61. As a preliminary coupling approach, Horner-Emmons reaction to produce the olefinic bond between the C11 and C12 positions afforded unsuccessful results, where both of phosphonates and aldehydes were decomposed under basic conditions required to activate the former segments.
62. G. Fráter, Helv. Chim. Acta, 62, 2829 (1979).
63. D. Romo, D. D. Johnson, L. Plamondon, T. Miwa, and S. L. Schreiber, J. Org. Chem., 57, 5060 (1992).
64. W. R. Roush, A. D. Palkowitz, and K. Ando, J. Am. Chem. Soc., 112, 6348 (1990).
65. An asymmetric process of this reaction was investigated, see: C. Chen, K. Tagami, and Y. Kishi, J. Org. Chem., 60, 5386 (1995).
66. 13C chemical shifts of the corresponding acetonides between the C13 and C15 positions [ D. A. Evans, D. L. Rieger, and J. R. Gage, Tetrahedron Lett., 31, 7099 (1990)].
67. a) Isolation from Siphonaria normalis: D. M. Roll, J. E. Biskupiak, C. L. Mayne, and C. M. Ireland, J. Am. Chem. Soc., 108, 6680 (1986);
68. b) Synthesis and absolute configuration: I. Paterson and M. V. Perkins, J. Am. Chem. Soc., 115, 1608 (1993); R. W. Hoffmann and G. Dahmann, Tetrahedron Lett., 34, 1115 (1993).
69. b) Synthesis and absolute configuration: I. Paterson and M. V. Perkins, J. Am. Chem. Soc., 115, 1608 (1993); R. W. Hoffmann and G. Dahmann, Tetrahedron Lett., 34, 1115 (1993).
70. a) Isolation from Siphonaria denticulata: J. E. Hochlowski, D. J. Faulkner, G. K. Matsumoto, and J. Clardy, J. Am. Chem. Soc., 105, 7413 (1983);
71. b) Biosynthesis: D. C. Manker, M. J. Garson, and D. J. Faulkner, J. Chem. Soc., Chem. Commun., 1988, 1061;
72. c) Synthesis and absolute configuration: F. E. Ziegler and M. R. Becker, J. Org. Chem., 55, 2800 (1990); M. W. Anderson, B. Hildebrandt, and R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 30, 97 (1991); M. W. Anderson, B. Hildebrandt, G. Dahmann, and R. W. Hoffmann, Chem. Ber., 124, 2127 (1991); I. Paterson and M. V. Perkins, Tetrahedron Lett., 33 801 (1992).
73. c) Synthesis and absolute configuration: F. E. Ziegler and M. R. Becker, J. Org. Chem., 55, 2800 (1990); M. W. Anderson, B. Hildebrandt, and R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 30, 97 (1991); M. W. Anderson, B. Hildebrandt, G. Dahmann, and R. W. Hoffmann, Chem. Ber., 124, 2127 (1991); I. Paterson and M. V. Perkins, Tetrahedron Lett., 33 801 (1992).
74. c) Synthesis and absolute configuration: F. E. Ziegler and M. R. Becker, J. Org. Chem., 55, 2800 (1990); M. W. Anderson, B. Hildebrandt, and R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 30, 97 (1991); M. W. Anderson, B. Hildebrandt, G. Dahmann, and R. W. Hoffmann, Chem. Ber., 124, 2127 (1991); I. Paterson and M. V. Perkins, Tetrahedron Lett., 33 801 (1992).
75. c) Synthesis and absolute configuration: F. E. Ziegler and M. R. Becker, J. Org. Chem., 55, 2800 (1990); M. W. Anderson, B. Hildebrandt, and R. W. Hoffmann, Angew. Chem., Int. Ed. Engl., 30, 97 (1991); M. W. Anderson, B. Hildebrandt, G. Dahmann, and R. W. Hoffmann, Chem. Ber., 124, 2127 (1991); I. Paterson and M. V. Perkins, Tetrahedron Lett., 33 801 (1992).
76. I. Paterson and R. D. Tillyer, Tetrahedron Lett., 33, 4233 (1992).
77. D. A. Evans and A. H. Hoveyda, J. Am. Chem. Soc., 112, 6447 (1990).
78. K. Nakanishi, N. Berova, and R. W. Woody, "Circular Dichroism," VCH, New York (1994).