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Natural product reports

Recent contributions from the asymmetric aza-Michael reaction to alkaloids total synthesis.


PMID 23896828

Abstract

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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47714
4-Formyl-1-methylpyridinium benzenesulfonate, ≥95.0%
C13H13NO4S