Development of new synthetic methods and its application to total synthesis of nitrogen-containing bioactive natural products

Chemical and Pharmaceutical Bulletin

Volumn 53, Issue 11, 2005, Pages 1375-1386

  Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Dendrobatid alkaloid; Incarvillateine; Marine alkaloid; New synthetic method; Nitrogen containing bioactive natural product; Total synthesis

Indexed keywords

ALKALOID DERIVATIVE; NITROGEN DERIVATIVE; PUMILIOTOXIN;

BIVALVE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DIMERIZATION; DRUG ISOLATION; DRUG SYNTHESIS; FROG; HUMAN; NONHUMAN; REVIEW; SPONGE (PORIFERA); STEREOCHEMISTRY;

ALKALOIDS; ANIMALS; BIOLOGICAL PRODUCTS; HUMANS; MARINE TOXINS; NITROGEN; PHARMACEUTICAL PREPARATIONS; RATS;

EID: 27744521817     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.53.1375     Document Type: Review

References (107)

1. For recent general reviews of Dendrobatid alkaloids, see: Daly J. W., Spande T. F., "Alkaloids: Chemical and Biological Perspectives," Vol. 4, ed. by Pelletier S. W., Wiley, New York, 1986, pp. 1-274.
2. For recent general reviews of Dendrobatid alkaloids, see: Daly J. W., Garraffo H. M., Spande T. F., "Alkaloids," Vol. 43, Chap. 3, ed. by Gordell G. A., Academic Press, San Diego, 1993, pp. 185-288.
3. For recent general reviews of Dendrobatid alkaloids, see: Daly J. W., "Alkaloids," Vol. 50, Chap. 4, ed. by Gordell G. A., Academic Press, San Diego, 1998, pp. 141-169.
4. For recent general reviews of Dendrobatid alkaloids, see: Daly J. W., Garraffo H. M., Spande T. F., "Alkaloids: Chemical and Biological Perspectives," Vol. 13, ed. by Pelletier S. W., Wiley, New York, 1999, pp. 1-161.
5. Ember L. R., Chem. Eng. News, 72, 16-17 (1994).
6. For a review of total syntheses of the pumiliotoxin and allopumiliotoxin alkaloids, see: Franklin A. S., Overman L. E., Chem. Rev., 96, 505-522 (1996).
7. For a review of total syntheses of the pumiliotoxin and allopumiliotoxin alkaloids, see: Kibayashi C., Aoyagi S., "Studies in Natural Products Chemistry," Vol. 19, ed. by Atta-ur-Rahman, Elsevier, Amsterdam, 1997, pp. 66-81.
8. Hirashima S., Aoyagi S., Kibayashi C., J. Am. Chem. Soc., 121, 9873-9874 (1999).
9. Aoyagi S., Hirashima S., Saito K., Kibayashi C., J. Org. Chem., 67, 5517-5526 (2002).
10. Danheiser R. L., Carini D. J., J. Org. Chem., 45, 3925-3927 (1980).
11. Danheiser R. L., Carini D. J., Kwasigroch C. A., J. Org. Chem., 51, 3870-3878 (1986).
12. 4 was used as a Lewis acid, a considerable drop in the yield (75%) of 14 was encountered.
13. Shishido Y., Kibayashi C., J. Org. Chem., 57, 2876-2883 (1992).
14. Negishi E., Valente L. F., Kobayashi M., J. Am. Chem. Soc., 102, 3298-3299 (1980).
15. For reviews of reaction of organozinc reagents, see: Erdik E., Tetrahedron, 48, 9577-9648 (1992).
16. For reviews of reaction of organozinc reagents, see: Knochel P., Singer R. D., Chem. Rev., 93, 2117-2188 (1993).
17. For other synthesis of pumiliotoxin B, see: Lin N.-H., Overman L. E., Rabinowitz M. H., Robinson L. A., Sharp M. J., Zablocki J., J. Am. Chem. Soc., 118, 9062-9072 (1996).
18. Aoyagi S., Wang T.-C., Kibayashi C., J. Am. Chem. Soc., 114, 10653-10654 (1992).
19. Aoyagi S., Wang T.-C., Kibayashi C., J. Am. Chem. Soc., 115, 11393-11409 (1993).
20. Kibayashi C., Pure Appl. Chem., 66, 2079-2082 (1994).
21. Takai K., Kimura K., Kuroda T., Hiyama T., Nozaki H., Tetrahedron Lett., 24, 5281-5284 (1983).
22. Takai K., Tagashira M., Kuroda T., Oshima K., Utimoto K., Nozaki H., J. Am. Chem. Soc., 108, 6048-6050 (1986).
23. Jin H., Uenishi J., Christ J., Kishi Y., J. Am. Chem. Soc., 108, 5644-5646 (1986).
24. For other syntheses of allopumiliotoxin A, see: Overman L. E., Robinson L. A., Zablocki J., J. Am. Chem. Soc., 114, 368-369 (1992).
25. For other syntheses of allopumiliotoxin A, see: Caderas C., Lett R., Overman L. E., Rabinowitz M. H., Robinson L. A., Sharp M. J., Zablocki J., J. Am. Chem. Soc., 118, 9073-9082 (1996).
26. For other syntheses of allopumiliotoxin A, see: Tang X.-Q., Montgomery J., J. Am. Chem. Soc., 122, 6950-6954 (2000).
27. Yamada H., Aoyagi S., Kibayashi C., J. Am. Chem. Soc., 118, 1054-1059 (1996).
28. Drautz H., Zähner H., Kupfer E., Keller-Schierlein W., Helv. Chim. Acta, 64, 1752-1765 (1981).
29. Glabley S., Kluge H., Hoppe H.-U., Angew. Chem., Int. Ed. Engl., 26, 664-665 (1987).
30. For the pioneering synthetic studies toward streptazolin, see: Kozikowski A. P., Park P., J. Am. Chem. Soc., 107, 1763-1765 (1985).
31. For the pioneering synthetic studies toward streptazolin, see: Flann C. J., Overman L. E., J. Am. Chem. Soc., 109, 6115-6118 (1987).
32. Ohwada J., Inoue Y., Kimura M., Kakisawa H., Bull. Chem. Soc. Jpn., 63, 287-289 (1990).
33. Kim S., Ahn K. H., J. Org. Chem., 49, 1717-1724 (1984).
34. For a review of palladium-catalyzed cycloisomeization of enynes, see: Trost B. M., Acc. Chem. Res., 23, 34-42 (1990).
35. Matsumura Y., Aoyagi S., Kibayashi C., Org. Lett., 5, 3249-3252 (2003).
36. Matsumura Y., Aoyagi S., Kibayashi C., Org. Lett., 6, 965-968 (2004).
37. Kuramoto M., Tong C., Yamada K., Chiba T., Hayashi Y., Uemura D., Tetrahedron Lett., 37, 3867-3870 (1996).
38. Arimoto H., Hayakawa I., Kuramoto M., Uemura D., Tetrahedron Lett., 39, 861-862 (1998).
39. Chou T., Kuramoto M., Otani Y., Shikano M., Yazawa K., Uemura D., Tetrahedron Lett., 37, 3871-3874 (1996).
40. Feldman K. S., Perkins A. L., Masters K. M., J. Org. Chem., 69, 7928-7932 (2004) and references cited therein.
41. For the synthesis of halichlorine, see: Trauner D., Danishefsky S. J., Tetrahedron Lett., 40, 6513-6516 (1999).
42. For the synthesis of halichlorine, see: Trauner D., Schwarz J. B., Danishefsky S. J., Angew. Chem., Int. Ed., 38, 3542-3545 (1999).
43. For the synthesis of halichlorine, see: Trauner D., Churchill D. G., Danishefsky S. J., Helv. Chim. Acta, 83, 2344-2351 (2000).
44. For the synthesis of pinnaic acid, see: Carson M. W., Kim G., Hentemann M. F., Trauner D., Danishefsky S. J., Angew. Chem., Int. Ed., 40, 4450-4452 (2001).
45. For the synthesis of pinnaic acid, see: Carson M. W., Kim G., Danishefsky S. J., Angew. Chem., Int. Ed., 40, 4453-4456 (2001).
46. Keck G. E., Webb R. R., II, J. Am. Chem. Soc., 103, 3173-3177 (1981).
47. For our own achievements in the development of the intramolecular acylnitroso-Diels-Alder approach for the synthesis of nitrogen-containing natural products, see: Kibayashi C., Aoyagi S., Synlett, 1995, 873-879 (1995).
48. For application of LiNH2BH3 for lactam ring opening, see: Aoyagi S., Tanaka R., Naruse M., Kibayashi C., J. Org. Chem., 63, 8397-8406 (1998).
49. For recent reviews on marine natural products, see: Davidson B. S., Chem. Rev., 93, 1771-1791 (1993).
50. For recent reviews on marine natural products, see: Faulkner D. J., Nat. Prod. Rep., 11, 355-394 (1994).
51. For recent reviews on marine natural products, see: Faulkner D. J., Nat. Prod. Rep., 12, 223-269 (1995).
52. For recent reviews on marine natural products, see: Faulkner D. J., Nat. Prod. Rep., 13, 75-125 (1996).
53. For recent reviews on marine natural products, see: Faulkner D. J., Nat. Prod. Rep., 15, 113-158 (1998).
54. For recent reviews on marine natural products, see: Faulkner D. J., Nat. Prod. Rep., 16, 155-198 (1999).
55. Blackman A. J., Li C., Hockless D. C. R., Skelton B. W., White A. H., Tetrahedron, 49, 8645-8656 (1993).
56. Li C., Blackman A. J., Aust. J. Chem., 47, 1355-1361 (1994).
57. Li C., Blackman A. J., Aust. J. Chem., 48, 955-965 (1995).
58. Biard J. F., Guyot S., Roussakis C., Verbist J. F., Vercauteren J., Weber J. F., Boukef K., Tetrahedron Lett., 35, 2691-2694 (1994).
59. Juge M., Grimaud N., Biard J. F., Sauviat M. P., Nabil M., Verbist J. F., Petit J. Y., Toxicon, 39, 1231-1237 (2001).
60. Patil A. D., Freyer A. J., Reichwein R., Cartre B., Killmer L. B., Faucette L., Johnson R. K., Faulkner D. J., Tetrahedron Lett., 38, 363-364 (1997).
61. Snider B. B., Liu T., J. Org. Chem., 62, 5630-5633 (1997).
62. Abe H., Aoyagi S., Kibayashi C., Tetrahedron Lett., 41, 1205-1208 (2000).
63. Abe H., Aoyagi S., Kibayashi C., J. Am. Chem. Soc., 122, 4583-4592 (2000).
64. Abe H., Aoyagi S., Kibayashi C., Angew. Chem., Int. Ed. Engl., 41, 3017-3020 (2002).
65. Abe H., Aoyagi S., Kibayashi C., J. Am. Chem. Soc., 127, 1473-1480 (2005).
66. For brief reviews on the synthesis of lepadiformine and related tricyclic marine alkaloids, see: Weinreb S. M., Acc. Chem. Res., 36, 59-65 (2003).
67. For brief reviews on the synthesis of lepadiformine and related tricyclic marine alkaloids, see: Kibayashi C., Aoyagi S., Abe H., Bull. Chem. Soc. Jpn., 76, 2059-2074 (2003).
68. Mitsunobu O., Synthesis, 1981, 1-28 (1981).
69. For a discussion of the solvent effect on stereochemical outcome of directed catalytic hydrogenation, see: Thompson H. W., McPherson E., Lences B. L., J. Org. Chem., 41, 2903-2906 (1976).
70. Tamura Y., Kawasaki T., Adachi M., Tanio M., Kita Y., Tetrahedron Lett., 1977, 4417-4420 (1977).
71. Burski J., Kieszkowski J., Michalski J., Pakulski M., Skowronska A., Tetrahedron, 39, 4175-4181 (1983).
72. This procedure was based upon the following: Sliwska H.-R., Liaaen-Jensen S., Tetrahedron: Asymmetry, 4, 361-368 (1993).
73. Werner K. M., De los Santos J. M., Weinreb S. M., Shang M., J. Org. Chem., 64, 686-687 (1999).
74. Werner K. M., De los Santos J. M., Weinreb S. M., Shang M., J. Org. Chem., 64, 4865-4873 (1999).
75. Pearson W. H., Barta N. S., Kampf J. W., Tetrahedron Lett., 38, 3369-3372 (1997).
76. Pearson W. H., Ren Y., J. Org. Chem., 64, 688-689 (1999).
77. Many attempts at obtaining a crystalline derivative of natural lepadiformine (provided by Professor Biard as an oil) suitable for X-ray crystallography were unsuccessful (W. Pearson, personal communication).
78. Sun P., Sun C., Weinreb S. M., Org. Lett., 3, 3507-3510 (2001).
79. Greshock T. J., Funk R. L., Org. Lett., 3, 3511-3514 (2001).
80. Schoemaker H. E., Speckamp W. N., Tetrahedron Lett., 1978, 1515-1518 (1978).
81. Schoemaker H. E., Speckamp W. N., Tetrahedron Lett., 1978, 4841-4844 (1978).
82. Schoemaker H. E., Speckamp W. N., Tetrahedron, 36, 951-958 (1980).
83. Evans D. A., Thomas E. W., Tetrahedron Lett., 1979, 411-414 (1979).
84. 81)
85. Noyori R., Tomino I., Tanimoto Y., J. Am. Chem. Soc., 101, 3129-3131 (1979).
86. For another total synthesis of (-)-lepadiformine and assignment of the absolute configuration of the natural product, see: Sun P., Sun C., Weinreb S. M., J. Org. Chem., 67, 4337-4345 (2002).
87. For synthesis of (-)-cylindricine C, see: Molander G. A., Rönn M., J. Org. Chem., 64, 5183-5187 (1999).
88. For syntheses of (+)-cylindricine C, see: Trost B. M., Rudd M. T., Org. Lett., 5, 4599-4602 (2003).
89. For syntheses of (+)-cylindricine C, see: Arai T., Abe H., Aoyagi S., Kibayashi C., Tetrahedron Lett., 45, 5921-5924 (2004).
90. For syntheses of other cylindricine alkaloids, see: (±)- Cylindricine A, D, and E: ref. 61.
91. For syntheses of other cylindricine alkaloids, see: (±)- Cylindricine A and B: Liu J. F., Heathcock C. H., J. Org. Chem., 64, 8263-8266 (1999).
92. For syntheses of other cylindricine alkaloids, see: (+)-Cylindricine D and E: ref. 88.
93. Maeng J.-H., Funk R. L., Org. Lett., 4, 331-333 (2002).
94. Fenster M. D. B., Dake G. R., Org. Lett., 5, 4313-4316 (2003).
95. Freyer A. J., Personal communication.
96. Ichikawa M., Aoyagi S., Kibayashi C., Tetrahedron Lett., 46, 2327-2329 (2005).
97. Ichikawa M., Aoyagi S., Kibayashi C., J. Am. Chem. Soc., 126, 16553-16558 (2004).
98. Chi Y.-M., Yan W.-M., Li J.-S., Phytochemistry, 29, 2376-2378 (1990).
99. Nakamura M., Chi Y.-M., Yan W.-M., Nakasugi Y., Yoshizawa T., Irino N., Hashimoto F., Kinjo J., Nohara T., Sakurada S., J. Nat. Prod., 62, 1293-1294 (1999).
100. Chi Y.-M., Hashimoto F., Nohara T., Yan W.-M., Sakurada S., Nakamura M., Minagawa Y., Yoshizawa T., 117th Annual Meeting of the Pharmaceutical Society of Japan, Tokyo, March 1997, Abstract 2, p. 147.
101. Chi Y.-M., Hashimoto F., Yan W.-M., Nohara T., Phytochemistry, 39, 1485-1487 (1995).
102. Chi Y.-M., Yan W.-M., Chen D.-C., Noguchi H., Iitaka Y., Sankawa I., Phytochemistry, 31, 2930-2932 (1992).
103. Nakamura M., Chi Y.-M., Yan W.-M., Yonezawa A., Nakasugi Y., Yoshizawa T., Hashimoto F., Kinjo J., Nohara T., Sakurada S., Planta Med., 67, 114-117 (2001).
104. For a review on "three-component coupling," see: Noyori R., Suzuki M., Angew. Chem., Int. Ed. Engl., 23, 847-876 (1984).
105. For an extensive review of synthetic application of intramolecular enone-olefin photocycloadditions, see: Crimmins M. T., Chem. Rev., 88, 1453-1473 (1988).
106. For a review of reduction with samarium(II) iodide, see: Molander G. A., Org. React., 46, 211-367 (1994).
107. Takahashi M., Ichikawa M., Aoyagi S., Kibayashi C., Tetrahedron Lett., 46, 57-59 (2005).