Natural Product Reports 2013-09-01

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

Zacharias Amara, Joachim Caron, Delphine Joseph

Index: Nat. Prod. Rep. 30(9) , 1211-25, (2013)

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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.