Radical cyclization in heterocycle synthesis. II. Total synthesis of (±)-anantine and (±)-isoanantine

Chemical and Pharmaceutical Bulletin

Volumn 45, Issue 12, 1997, Pages 1932-1939

  Naito, Takeaki ^a   Honda, Yuko ^a   Bhavakul, Vanida ^a   Yamaguchi, Sayaka ^a   Fujiwara, Azusa ^a   Miyata, Okiko ^a   Ninomiya, Ichiya ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Anantine; Imidazole alkaloid; Radical cyclization; Selenium; Sulfur; Total synthesis

Indexed keywords

ALKALOID; ANANTINE; HERBACEOUS AGENT; ISOANANTINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0031456959     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.45.1932     Document Type: Article

References (16)

1. Preliminary communication: Naito T., Honda Y., Miyata O., Ninomiya I., Chem. Pharm. Bull., 41, 217-219 (1993).
2. Naito T., Honda Y., Miyata O., Ninomiya I., J. Chem. Soc., Perkin Trans., 1, 1995, 19-26.
3. a) Tchissambou L., Benechie M., Khuong-Huu F., Tetrahedron, 38, 2687-2695 (1982);
4. b) Idem, Tetrahedron Lett., 1978, 1801-1802;
5. Khuong-Huu F., Monseur X., Ratle G., Lukacs G., Goutarel, ibid, 1973, 1757-1760;
6. Chiaroni A., Riche C., Tchissambou L., Khuong-Huu F., J. Chem. Res. Synop., 1981, 182;
7. e) Waterman P. G., Faulkner D. F., Phytochemistry, 20, 2765-2767 (1981);
8. f) Maat L., Beyerman H. C., "The Alkaloids," Vol. XXII, ed. by Brossi A., Academic Press, Inc., New York, p. 281.
9. Fishwick C. W. G., Foster R. J., Carr R. E., Tetrahedron Lett., 37, 3915-3918 (1996).
10. Sato T., Wada Y., Nishimoto M., Ishibashi H., Ikeda M., J. Chem. Soc., Perkin Trans. 1, 1989, 879-886.
11. van Leusen A. M., Schaart F. J., van Leusen D., Recl. Trav. Chim. Pays-Bas, 98, 258-262 (1979).
12. Carbon J. A., J. Am. Chem. Soc., 80, 6083-6088 (1958).
13. Bettoni G., Cellucci C., Tortorella V., J. Heterocycl. Chem., 13, 1053-1055 (1976).
14. Tsuge O., Kanemasa S., Hatada A., Matsuda K., Bull. Chem. Soc. Jpn., 59, 2537-2545 (1986).
15. Kusuda S., Ueno Y., Hagiwara T., Toru T., J. Chem. Soc., Perkin Trans. 1, 1993, 1981-1988.
16. Pollini G. P., Barco A., Giuli De G., Synthesis, 1972, 44-45.