Journal
NATURAL PRODUCT REPORTS
Volume 30, Issue 9, Pages 1211-1225Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c3np20121j
Keywords
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Funding
- French Ministry of Superior Education and Research
- University Paris-Sud 11
- CNRS
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This review focuses on recent applications of the aza-Michael reaction in alkaloids total synthesis with a special emphasis on stereoselectivity. The report highlights achievements and challenges over the past five years and describes stereoselective intra- and inter-molecular conjugate addition of nitrogen-containing nucleophiles, including tandem and cascade processes. Total asymmetric syntheses of natural scaffolds, such as pyrrolidine, piperidine and izidine families, are depicted. Multi-step syntheses of highly challenging natural products are further detailed, assessing the scope of the stereocontrolled aza-Michael reaction as a powerful tool in alkaloid chemistry.
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