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Updated: Aug 12, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
The first total synthesis of natural grenadamide
Thomas D Avery1, Julie A Culbert, Dennis K Taylor
1Department of Chemistry, University of Adelaide, South Australia 5005, Australia.
Abstract:
A concise, high yielding route to the naturally occurring enantiomer of grenadamide utilizing a 3,6-disubstituted 1,2-dioxine starting material is presented. The route allows for ease in synthesizing grenadamide derivatives varying at cyclopropyl carbons 2 and 3, with access to both enantiomers. Evidence for phosphorus-assisted deprotonation of 1,2-dioxines is also discussed.
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