Back to Search Start Over

Short total synthesis of (+/-)-sceptrin.

Authors :
Baran PS
Zografos AL
O'Malley DP
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