Journal
MOLECULES
Volume 27, Issue 13, Pages -Publisher
MDPI
DOI: 10.3390/molecules27134141
Keywords
narciclasine; Amaryllidaceae alkaloids; Semi-synthesis; natural products
Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Research Chair Program
- Canada Foundation for Innovation (CFI)
- TDC Research Foundation
- Ontario Partnership for Innovation and Commercialization (OPIC)
- Advanced Biomanufacturing Centre (Brock University)
- National Institutes of Health [1R15CA227680-01A1]
- TDC Research, Inc.
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This article presents a method for synthesizing C-1 analogues of narciclasine, in which natural narciclasine is protected and converted to its C-1 enol derivative using a novel semi-synthetic route. The converted compound underwent further reactions and evaluation for cytotoxic activity.
During the search for a general, efficient route toward the synthesis of C-1 analogues of narciclasine, natural narciclasine was protected and converted to its C-1 enol derivative using a novel semi-synthetic route. Attempted conversion of this material to its triflate in order to conduct cross-coupling at C-1 resulted in a triflate at C-6 that was successfully coupled with several functionalities. Four novel compounds were fully deprotected after seven steps and subjected to evaluation for cytotoxic activity against three cancer cell lines. Only one derivative showed moderate activity compared to that of narciclasine. Spectral and physical data are provided for all new compounds.
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