Highlights from 43 years of chemistry of naturally occurring nitrogen-containing heterocycles. (1). Syntheses and structure determinations of benzo[a]quinolizidine-type and indolo[2,3-a]quinolizidine-type alkaloids isolated from several plants

Yakugaku Zasshi

Volumn 116, Issue 5, 1996, Pages 335-354

  Fujii, Tozo ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

Absolute configuration; Alangium alkaloid; Benzo quinolizidine alkaloid; Cincholoipon; Indolo 2,3 quinolizidine alkaloid; Total synthesis

Indexed keywords

ALKALOID; BENZO[A]QUINOLIZIDINE DERIVATIVE; INDOLO[2,3 A]QUINOLIZIDINE DERIVATIVE; PLANT EXTRACT; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

CHIRALITY; DRUG ISOLATION; DRUG SYNTHESIS; PLANT; RACEMIC MIXTURE; REVIEW; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ALKALOIDS; INDOLES; MOLECULAR CONFORMATION; QUINOLIZINES; STEREOISOMERISM;

EID: 0029896455     PISSN: 00316903     EISSN: None     Source Type: Journal    
DOI: 10.1248/yakushi1947.116.5_335     Document Type: Review

References (101)

1. Kirtikar K. R., Basu B. D., "Indian Medicinal Plants," 2nd ed., Vol. II, L. M. Basu, Allahabad, India, 1933, pp. 1236-1239.
2. Chopra R. N., Chopra I. C., Handa K. L., Kapur L. D., "Indigenous Drugs of India," 2nd ed., U. N. Dhar and Sons, Calcutta, India, 1958, pp. 270-271.
3. Dasgupta B., J. Pharm. Sci., 54, 481-483 (1965).
4. a) Fujii T., Ohba M., "The Alkaloids," Vol. XXII, ed. by Brossi A., Academic Press, New York, 1983, Chapter 1
5. c) Wiegrebe W., Kramer W. J., Shamma M., J. Nat, Prod., 47, 397-408 (1984)
6. d) Fujii T., Ohba M., Yoshifuji S., Heterocycles, 27, 1009-1033 (1988)
7. e) A. lamarckii 3-O-demethyl-2-O-methylalangiside Itoh A., Tanahashi T., Nagakura N., Nayeshiro H., Phytochemistry, 36, 383-387 (1994)
8. f)isoalangiside, 3-0-demethyl-2-O-methylisoalangiside, methylisoalangiside Itoh A., Tanahashi T., Nagakura N., Chem. Pharm. Bull., 42, 2208-2210 (1994)
9. h) Alangium bussyanum: Diallo A. O., Mehri H., Iouzalen L., Plat M., Phytochemistry, 40, 975-977 (1995).
10. a) Brossi A., Teitel S., Parry G. V., "The Alkaloids," Vol., XIII, ed. by Manske R. H. F., Academic Press, New York, 1971, Chapter 3
11. b) Openshaw H. T., "Chemistry of the Alkaloids," ed. by Pelletier S. W., Van Nostrand Reinhold Co., New York, 1970, Chapter 4
12. c) Shamma M., "The Isoquinoline Alkaloids," Academic Press, New York, 1972, Chapter 23
13. d) Kametani T., "The Chemistry of the Isoquinoline Alkaloids," Vol. 2, Kinkodo, Sendai, 1974, Chapter 18
14. e) Shamma M., Moniot J. L., "Isoquinoline Alkaloids Research, 1972-1977," Plenum Press, New York, 1978, Chapter 27.
15. b) Idem, ibid., 29, 249-251 (1993).
16. a) Fujii T., Yoshifuji S., Tai M., Chem. Pharm. Bull., 23, 2094-2103 (1975)
17. b) Fujii T., Yoshifuji S., ibid., 26, 2253-2257 (1978)
18. c) Fujii T., Kogen H., Yoshifuji S., Iga K., ibid., 27, 1847-1856 (1979)
19. a) Sugasawa S., Fujii T., Proc. Jpn. Acad., 30, 877-882 (1954)
20. b) Idem, Chem. Pharm. Bull., 3, 47-52 (1955)
21. Fujii T., ibid., 6, 591-601 (1958).
22. a) Fujii T., Yoshifuji S., Ohba M., Chem. Pharm. Bull., 26, 645-649 (1978)
23. b) Fujii T., Yoshifuji S., Ikeda K., ibid., 27, 2841-2845 (1979).
24. Fujii T., Yoshifuji S., Yamada K., Chem. Pharm. Bull., 26, 2071-2080 (1978).
25. Fujii T., Yoshifuji S., Chem. Pharm. Bull., 27, 1486-1490 (1979).
26. Fujii T., Yoshifuji S., Yamada K., Tetrahedron, 36, 965-968 (1980).
27. Fujii T., Yamada K., Minami S., Yoshifuji S., Ohba M., Chem. Pharm. Bull., 31, 2583-2592 (1983).
28. Fujii T., Kogen H., Yoshifuji S., Ohba M., Chem. Pharm. Bull., 33, 1946-1954 (1985).
29. Fujii T., Ohba M., Chem. Pharm. Bull., 33, 144-151 (1985).
30. Ohba M., Hayashi M., Fujii T., Chem. Pharm. Bull., 33, 3724-3730 (1985).
31. Fujii T., Ohba M., Chem. Pharm. Bull., 33, 4314-4319 (1985).
32. Fujii T., Ohba M., Ali E., Suzuki H., Sakaguchi J., Chem. Pharm. Bull., 35, 2755-2760 (1987).
33. Fujii T., Ohba M., Yonezawa A., Sakaguchi J., Chem. Pharm. Bull., 35, 3470-3474 (1987).
34. Fujii T., Yoshifuji S., Chem. Pharm. Bull., 27, 2497-2501 (1979).
35. Weber H., "Advances in Heterocyclic Chemistry," Vol. 41, ed. by Katritzky A. R., Academic Press, New York, 1987, pp. 275-317.
36. a) Möhrle H., Weber H., Tetrahedron, 26, 2953-2958 (1970)
37. b) Idem, Chem. Ber., 104, 1478-1489 (1971).
38. Abramovitch R. A., Vinutha A. R., J. Chem. Soc. (B), 1971, 131-136.
39. Fujii T., Yoshifuji S., Michishita K., Mitsukuchi M., Yoshida K., Chem. Pharm. Bull., 21, 2695-2704 (1973).
40. Fujii T., Yoshifuji S., Yoshida K., Ohba M., Ikegami S., Kirisawa M., Chem. Pharm. Bull., 23, 993-1002 (1975).
41. Fujii T., Yoshida K., Ohba M., Mitsukuchi M., Tanaka I., Yoshifuji S., Kirisawa M., Chem. Pharm. Bull., 25, 2072-2077 (1977).
42. Fujii T., Ohba M., Yoshifuji S., Kirisawa M., Chem. Pharm. Bull., 25, 2887-2894 (1977).
43. a) Fujii T., Hiraga T., Yoshifuji S., Ohba M., Yoshida K., Heterocycles, 10, 23-28 (1978)
44. b) Fujii T., Hiraga T., Ohba M., Chem. Pharm. Bull., 29, 2503-2508 (1981).
45. a) Möhrle H., Arch. Pharm. Ber. Dtsch. Pharm. Ges., 297, 474-487 (1964)
46. b) Knabe J., ibid., 292, 416-430 (1959).
47. Fujii T., Yoshida K., Ohba M., Yoshifuji S., Chem. Pharm. Bull., 25, 2336-2342 (1977).
48. Fujii T., Ohba M., Yoshifuji S., Chem. Pharm. Bull., 25, 3042-3048 (1977).
49. Fujii T., Hiraga T., Ohba M., Chem. Pharm. Bull., 29, 2691-2695 (1981).
50. Fujii T., Ohba M., Akiyama S., Chem. Pharm. Bull., 33, 5316-5327 (1985).
51. Fujii T., Ohba M., Sakaguchi J., Chem. Pharm. Bull., 35, 3628-3640 (1987).
52. Kaufmann A., Rothlin E., Brunnschweiler P., Ber. Dtsch. Chem. Ges., 49, 2299-2310 (1916).
53. Prelog V., Zalán E., Helv. Chim. Acta, 27, 535-545 (1944).
54. Fujii T., Yoshifuji S., Tetrahedron, 36, 1539-1545 (1980).
55. Jjj(fR41> IStScOiIUCTia 28%.
56. Cincholoipon methyl ester i±, jS-collidine (D methoxycarbonylation S.C/CD rf-tartaric acid : Uskoković M. R., Henderson T., Reese C., Lee H. L., Grethe G., Gutzwiller J., J. Am. Chem. Soc., 100, 571-576 (1978).
57. b Fujii T., Yoshifuji S., J. Org. Chem., 45, 1889-1893 (1980).
58. c Fujii T., Ohba M., Chem. Pharm. Bull., 33, 583-590 (1985).
59. d Fujii T., Ohba M., Suzuki H., Chem. Pharm. Bull., 33, 1023-1028 (1985).
60. a) Leonard N. J., Conrow K., Sauers R. R., J. Am. Chem. Soc., 80, 5185-5193 (1958)
61. b) Möhrle H., Arch. Pharm. Ber. Dtsch. Pharm. Ges., 299, 122-131 (1966)
62. c) Möhrle H., Weber H., Chem. Ber., 105, 368-376 (1972)
63. d) Fujii T., Yoshifuji S., Chem. Pharm. Bull., 20, 1451-1456 (1972).
64. Fujii T., Ohba M., Tsuchida M., Saito K., Hirano Y., Sakaguchi J., Chem. Pharm. Bull., 34, 496-507 (1986).
65. Fujii T., Ohba M., Akiyama S., Chem. Pharm. Bull., 33, 1716-1720 (1985).
66. Fujii T., Ohba M., Yoshifuji S., Akiyama S., Chem. Pharm. Bull., 33, 1062-1068 (1985).
67. Openshaw H. T., Whittaker N., J. Chem. Soc., 1963, 1461-1471.
68. a) Szántay C., Töke L., Kolonits P., J. Org. Chem., 31, 1447-1451 (1966)
69. b) Idem, Magy. Kern. Foly., 73, 293-298 (1967)
70. [Chem. Abstr., 68, 3044g (1968)].
71. Teitel S., Brossi A., J. Am. Chem. Soc., 88, 4068-4071 (1966).
72. Openshaw H. T., Whittaker N., J. Chem. Soc. (C), 1969, 91-94.
73. Battersby A. R., Harper B. J. T., J. Chem. Soc., 1959, 1748-1753.
74. Fujii T., Ohba M., Hatakeyama H., Chem. Pharm. Bull., 35, 2355-2359 (1987).
75. Fujii T., Ohba M., Chem. Pharm. Bull., 33, 5264-5269 (1985).
76. Popelak A., Haack E., Spingler H., Tetrahedron Lett., 1966, 1081-1085.
77. Fujii T., Ohba M., Yoneyama K., Kizu H., Chem. Pharm. Bull., 33, 358-361 (1985).
78. Fujii T., Ohba M., Yoneyama K., Kizu H., Yoshifuji S., Chem. Pharm. Bull., 34, 669-676 (1986).
79. Fujii T., Ohba M., Shimohata K., Yoshifuji S., Heterocycles, 26, 2949-2957 (1987).
80. a) Johns S. R., Lamberton J. A., Occolowitz J. L., Chem. Commun., 1966, 421-422
81. b) Idem, Aust. J. Chem., 19, 1951-1954 (1966).
82. Fujii T., Yoshifuji S., Ito H., Chem. Pharm. Bull., 36, 3348-3353 (1988).
83. Fujii T., Ohba M., Tachinami T., Miyajima H., Chem. Pharm. Bull., 38, 1200-1204 (1990).
84. Fujii T., Ohba M., Tachinami T., Ohashi T., Chem. Pharm. Bull., 39, 75-78 (1991).
85. [Lactim ether -vincamine : Govindachari T. R., Rajeswari S., Indian J. Chem., 22B, 531-537 (1983).
86. Ohba M., Ohashi T., Fujii T., Heterocycles, 32, 319-328 (1991).
87. Fujii T., Ohba M., Ohashi T., Tetrahedron, 49, 1879-1890 (1993).
88. Fujii T., Ohba M., Seto S., Chem. Pharm. Bull., 43, 49-52 (1995).
89. Fujii T., Ohba M., Sasaki N., Chem. Pharm. Bull., 37, 2822-2824 (1989).
90. Schuij C., Beijersbergen van Henegouwen M. J., Gerritsma K. W., J. Chem. Soc., Perkin Trans. 1, 1979, 970-975.
91. Fujii T., Ohba M., Yonemitsu O., Ban Y., Chem. Pharm. Bull., 30, 598-609 (1982).
92. Comforth J. W., Aust. J. Chem., 46, 157-170 (1993).
93. Fujii T., Ohba M., Chem. Pharm. Bull., 36, 2665-2668 (1988).