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Short total synthesis of (+/-)-sceptrin.
- Source :
-
Journal of the American Chemical Society [J Am Chem Soc] 2004 Mar 31; Vol. 126 (12), pp. 3726-7. - Publication Year :
- 2004
-
Abstract
- Gifted with novel chemical features and extraordinary biological activity, sceptrin has remained a prominent unanswered synthetic challenge since its characterization in 1981 by Faulkner and Clardy. A concise and practical solution to the myriad of chemical challenges posed by sceptrin is reported in this Communication. Thus, through a sequence involving rearrangement of an oxaquadricyclane, a new method for chemo- and regioselective halogenation, a mild sequence for 2-aminoimidazole formation, and careful synthetic choreography, (+/-)-sceptrin is obtained in a minimum of steps and in 24% overall yield from dimethyl acetylenedicarboxylate without a single use of chromatography.
Details
- Language :
- English
- ISSN :
- 0002-7863
- Volume :
- 126
- Issue :
- 12
- Database :
- MEDLINE
- Journal :
- Journal of the American Chemical Society
- Publication Type :
- Academic Journal
- Accession number :
- 15038721
- Full Text :
- https://doi.org/10.1021/ja049648s