Iron-catalyzed enediene carbocyclizations. The total synthesis of (-)-gibboside

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8417-8420

  Takacs, James M ^a   Vayalakkada, Suresh ^a   Mehrman, Steven J ^a   Kingsbury, Celia L ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOPENTANE DERIVATIVE; GIBBOSIDE; IRIDOID; IRON; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0037064472     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01662-3     Document Type: Article

References (24)

1. Uesato S., Shan X., Inouye H., Shingu T., Inoue M., Doi M. Phytochemistry. 26:1987;561-564.
2. Ghisalberti E.L. Phytomedicine. 5:1998;147-163.
3. Mandal S., Jain R., Mukhopadhyay S. Indian J. Pharm. Sci. 60:1998;123-127.
4. Xie S., Uesato S., Fujita T., Inouye H. J. Nat. Prod. 52:1989;701-705.
5. Sampaio-Santos M.I., Kaplan M.A.C. J. Braz. Chem. Soc. 12:2001;144-153.
6. Franzyk H. Prog. Chem. Org. Nat. Prod. 79:2000;1-114.
7. Nangia A., Prasuna G., Rao P.B. Tetrahedron. 53:1997;14507-14545.
8. Isoe S. Stud. Nat. Prod. Chem. 16:1995;289-320.
9. Takacs J.M., Weidner J.J., Takacs B.E. Tetrahedron Lett. 34:1993;6219-6222.
10. Takacs J.M., Myoung Y.-C., Anderson L.G. J. Org. Chem. 59:1994;6928-6942.
11. Takacs J.M., Weidner J.J., Newsome P.W., Takacs B.E., Chidambaram R., Shoemaker R.K. J. Org. Chem. 60:1995;3474-3486.
12. Takacs J.M., Boito S.C. Tetrahedron Lett. 36:1995;2941-2944.
13. Takacs J.M., Myoung Y.-C. Tetrahedron Lett. 33:1992;317-320.
14. Takacs J.M., Boito S.C., Myoung Y.-C. Curr. Org. Chem. 2:1998;233-254.
15. Takacs J.M., Jaber M.R., Swanson B.J., Mehrman S.J. Tetrahedron: Asymmetry. 9:1998;4313-4324.
16. Evans D.A., Sjogren E.B., Bartroli J., Dow R.L. Tetrahedron Lett. 27:1986;4957-4960.
17. Crimmins M.T., Tabet E.A. J. Org. Chem. 66:2001;4012-4018.
18. Bonadies F., Cardilli A., Lattanzi A., Orelli L.R., Scettri A. Tetrahedron Lett. 35:1994;3383-3386.
19. Takacs J.M., Jaber M.R., Clement F., Walters C. J. Org. Chem. 63:1998;6757-6760.
20. Takano S., Akiyama M., Sato S., Ogasawara K. Chem. Lett. 1983;1593-1596.
21. CAS registry number: 239103-32-3.
22. Horita K., Yoshioka T., Tanaka T., Oikawa Y., Yonemitsu O. Tetrahedron. 42:1986;3021-3028.
23. Schmidt R.R., Michel J. Angew. Chem., Int. Ed. 19:1980;731-732.
24. 9 (M+ plus Na) 385.1467, found 385.1471 m/z.