Macrocyclic compounds with enediyne motif

Glavaš, Mladena; Gredičak, Matija; Jerić, Ivanka Macrocyclic compounds with enediyne motif. In: The 22nd International Conference on Organic Synthesis Book of abstracts (16 September 2018 - 21 September 2018) Florence, Italy. (Unpublished)

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Abstract

Multicomponent reactions (MCRs) are powerful tool for introducing chemical diversity and the rapid generation of small-molecule libraries.[1] The main advantage of MCRs is an easy access to libraries of complex and structurally diverse compounds in a single reaction step starting from relatively simple components. Isocyanide-based multicomponent reactions (IMCRs, i.e. Passerini, Ugi reaction) are among the most important MCRs. The Ugi reaction provides a rapid route to peptide-like compounds through coupling of an aldehyde, an amine, a carboxylic acid and an isocyanide. The Ugi reaction can be coupled with a post-condensation reactions, like cyclisation, to increase the number of compounds available for screening.[2] Our aim was synthesis of macrocycle compounds with enediyne motif utilizing the Ugi reaction/Sonogashira reaction approach coupled with intramolecular cyclisation (Scheme 1). The enediyne structural motif was found in natural products with strong anticancer activity.[3] Additionally, enediyne compounds can be used in asymmetric hydrogenation reactions[4] and in metal complexation.[5] The Ugi reaction of aldehyde 1,different C-protected amino acids, commercially available isocyanides and carboxylic acids gave Ugi products 2. Next, the Sonogashira reaction was carried out with 2 unsaturated alcohols yielding acyclic structures 3 and 4. Finally, macrocycle compounds 5 and 6 were synthesized by intramolecular esterification (Scheme 1).

Item Type:	Unpublished conference/workshop items or lecture materials
Uncontrolled Keywords:	multicomponent reactions; Ugi and Passerini reaction; Sonogashira reaction
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry NMR Center
Depositing User:	Mladena Glavaš
Date Deposited:	19 Dec 2025 07:18
URI:	http://fulir.irb.hr/id/eprint/10592

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