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Updated: Jun 24, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Total synthesis of ouabagenin and ouabain
Maddi Sridhar Reddy1, Hongxing Zhang, Serge Phoenix
1Laboratoire de Synthèse Organique, Département de Chimie, Institut de Pharmacologie de Sherbrooke, Université de Sherbrooke, Sherbrooke, Québec J1H 5N4, Canada.
Abstract:
A full account of the total synthesis of ouabagenin and ouabain is described. A highly stereocontrolled anionic cycloaddition for the rapid construction of the basic steroid skeleton is a pivotal conversion for the whole strategy. A careful study was needed to establish the order and the sequence of functional group manipulations. Specific conformational features of the ouabain skeleton allowed us to overcome a few stereochemical problems. Degradation studies on ouabain provided an ultimate proof for a key intermediate, which is used as a relay. Late stage butenolide formation and glycosidation yielded ouabain.
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