A convenient method for retro-cycloaddition of adducts from steroidal 5,7-dienes and 4-phenyl-1,2,4-triazolidine-3,5-dione and application to the syntheses of biosynthetic intermediates of ergosterol

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 9, 1998, Pages 1454-1458

  Tachibana, Yoji ^a  

^a NISSHIN SEIFUN GROUP INC   (Japan)

Author keywords

1,8 diazabicyclo 5.4.0 undec 7 ene; 4 phenyl 1,2,4 triazolidine 3,5 dione; Protection deprotection; Retro cycloaddition; Steroidal 5,7 diene

Indexed keywords

1,8 DIAZABICYCLO[5.4.0]UNDEC 7 ENE; 4 PHENYL 1,2,4 TRIAZOLIDINE 3,5 DIONE; ALKADIENE; ERGOSTEROL; UNCLASSIFIED DRUG; VITAMIN D DERIVATIVE;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STEROIDOGENESIS;

EID: 0031666228     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1454     Document Type: Article

References (27)

1. Barton D. H. R., Shioiri T., Widdowson D. A., J. Chem. Soc., Chem. Commun., 1970, 939-940.
2. Kondo F., Miyashita M., Konno K., Takayama H., J. Chem. Soc., Perkin Trans. 1, 1995, 2679-2680.
3. Tada M., Oikawa A., J. Chem. Soc., Chem. Commun., 1978, 727-728.
4. Barton D. H. R., Lusinchi X., Ramirez J. S., Tetrahedron Lett., 24, 2995-2998 (1983).
5. Kubodera N., Miyamoto K., Ochi K., J. Org. Chem., 57, 5019-5020 (1992).
6. Anastasia M., Derossi H., J. Chem. Soc., Chem. Commun., 1979, 164.
7. Tachibana Y., Tsuji M., Yokoyama S., Tejima T., J. Synth. Org. Chem., 55, 65-75 (1995).
8. a) Tachibana Y., Nippon Kagaku Kaishi, 1996, 91-96
9. b) Miyamoto K., Murayama E., Ochi K., Watanabe H., Kubodera N., Chem. Pharm. Bull., 41, 1111-1113 (1993).
10. Fryberg M., Oehlschlager A. C., Unrau A. M., J. Am. Chem. Soc., 95, 5747-5757 (1973).
11. a) Mirek J., Kawalek B., Tetrahedron, 26, 1261-1265 (1970)
12. b) Barton D. H. R., Kemple J. M., Widdowson D. A., J. Chem. Soc., Perkin Trans. 1, 1972, 513-522.
13. a) Tachibana Y., Yokoyama S., Tsuji M., Bull. Chem. Soc. Jpn., 62, 2599-2603 (1989)
14. b) Tachibana Y., Yokoyama S., Tejima T., Nippon Kagaku Kaishi, 1994, 345-353.
15. a) Barton D. H. R., Shioiri T., Widdowson D. A., J. Chem. Soc., (C), 1971, 1968-1974
16. b) Morzycki J. W., Schnoes H. K., DeLuca H. F., J. Org. Chem., 49, 2148-2151 (1984).
17. Choudhry S. C., Belica P. S., Coffen D. L., Focella A., Maehr H., Manchand P. S., Serico L., Yang R. T., J. Org. Chem., 58, 1496-1500 (1993).
18. Windaus A., Trautmann G., Z. Physiol. Chem., 247, 185-188 (1937).
19. Ruigh W. L., J. Am. Chem. Soc., 64, 1900-1902 (1942).
20. a) Tsuji, M., Yokoyama, S., Tachibana, Y., Bull. Chem. Soc., Jpn., 62, 3132-3137 (1989)
21. b) Idem., ibid., 63, 2233-2238 (1990).
22. Guest G. W., Williams D. H., J. Chem. Soc., Perkin Trans. 1, 1979, 1695-1697.
23. Tachibana Y., Nippon Kagaku Kaishi, 1992, 53-62.
24. Tachibana Y., Chem. Pharm. Bull., 42, 2215-2218 (1994).
25. Tachibana Y., Bull. Chem. Soc. Jpn., 61, 3915-3818 (1988).
26. Suga T., Ohta S., Ohmoto T., J. Chem. Soc., Perkin Trans. 1, 1987, 2845-848.
27. Breivih N. O., Owades J. L. Light R. F., J. Org. Chem., 19, 1734-1740 (1954).