Synthesis of Nature‐Inspired Medium‐Sized Fused Heterocycles from Amino Acids |
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Authors: | Dr. Pilar Ventosa‐Andrés Dr. Agustina La‐Venia Dr. Carlos Alfonso Barea Ripoll Dr. Ludmila Hradilová Dr. Viktor Krchňák |
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Affiliation: | 1. Department of Organic Chemistry, Palacky University771, 46 Olomouc (Czech Republic);2. Farmak, Na vl?inci 16/3, Klá?terní Hradisko, 779 00 Olomouc, 251 (Czech Republic);3. Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556 (United States) |
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Abstract: | Herein, we describe the synthesis of molecular scaffolds consisting of medium‐sized fused heterocycles using amino acids, which are some of the most useful building blocks used by nature as well as chemists to create structural diversity. The acyclic precursors were assembled by using traditional Merrifield solid‐phase peptide synthesis, and cyclization was carried out through acid‐mediated tandem endocyclic N‐acyliminium ion formation, followed by nucleophilic addition with internal nucleophiles. The synthesis of molecular scaffolds consisting of seven‐, eight‐, and nine‐membered rings proceeded with full stereocontrol of the newly generated stereogenic center in most cases. |
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Keywords: | cyclization drug discovery fused‐ring systems regioselectivity solid‐phase synthesis |
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