Synonyms:amauromine
98%Min *data from raw suppliers
Amauromine *data from reagent suppliers
The research describes the successful total synthesis of the dimeric alkaloid amauromine, a compound of interest due to its unique structure and biological activity as a vasodilator. The purpose of the study was to achieve the first total synthesis of amauromine using a convergent synthetic route based on the thio-Claisen rearrangement reaction through a sulphonium salt, starting from L-tryptophan. Key chemicals used in the synthesis include L-tryptophan, phosphorus pentasulfide, methyl iodide, dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (HOSu), potassium carbonate, prenyl bromide, titanium tetrachloride, and lithium aluminium hydride. The synthesis involved multiple steps, including oxidation, esterification, introduction of methylthio function, formation of the key intermediate diketopiperazine, thio-Claisen rearrangement, catalytic reduction, and reductive desulphurization. The final step involved concurrent cyclization and reductive desulphurization using TiCl4-LiAlH4 to obtain amauromine. The study concluded that the total synthesis was achieved with a yield of 15%, and the synthesized amauromine was identical to the natural compound in all respects, confirming the success of the synthetic route. This achievement supports the hypothesis on the mode of introduction of the inverted isoprene unit in related indole alkaloids and provides a potential pathway for the biosynthesis of amauromine.
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