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Updated: Feb 20, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Studies toward the Total Synthesis of Griseoviridin
Carolina Caso1, Karl-Heinz Altmann1
1Department of Chemistry and Applied Biosciences, Institute of Pharmaceutical Sciences, ETH Zürich, Vladimir-Prelog-Weg 4, CH-8093 Zürich, Switzerland.
Abstract:
The synthesis of bis-macrolactam 5 as an advanced intermediate for the projected total synthesis of griseoviridin (1) has been achieved via intramolecular Suzuki-Miyaura coupling (>70% yield). Further key steps were the construction of the C(17)-C(18) bond by a SmI2-mediated Barbier-type coupling, the establishment of the C(18) stereocenter by a diastereoselective Narasaka-Prasad reduction, and an electrophilic sulfur transfer to establish the S(1)-C(2) bond. DMP oxidation of 5 and deprotection gave griseoviridin analog 36 in 32% yield.
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