期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 75, 期 9, 页码 3069-3084出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo1003136
关键词
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资金
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program, Canada Foundation for Innovation (CFI)
- Research Corporation, TDC Research, Inc.
- Brock University
- Ontario Partnership for Innovation and Commercialization (OPIC)
- Lotte and John Hecht Memorial Foundation
- National Institutes of Health [P20 R R016480]
An efficient synthesis of C-1 derivatives of 7-deoxypancratistatin is reported. The key steps include the following: selective opening of an epoxide with aluminum acetylide in the presence of an aziridine; solid-state silica-gel-catalyzed opening of an aziridine; and oxidative cleavage of a phenanthrene core and its recyclization to phenanthridone to provide the key C-1 aldehyde 22. The conversion of this aldehyde to C-1 acetoxymethyl and C-1 hydroxymethyl derivatives is described along with the evaluation of their biological activity against several cancer cell lines and in an apoptosis study. The C-1 acetoxymethyl derivative has shown promising activity comparable to that of the natural product. In addition, a total synthesis of trans-dihydrolycoricidine and a formal total synthesis of 7-deoxypancratistatin are reported from aldehyde 22. Detailed experimental and spectral data are provided for all new compounds.
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