title: Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids.
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.
authors.affiliation: Department of Organic Chemistry, Palacky University771, 46 Olomouc (Czech Republic).
authors.forename: Pilar
authors.initials: P
authors.lastname: Ventosa-Andrés
authors.affiliation: Department of Organic Chemistry, Palacky University771, 46 Olomouc (Czech Republic).
authors.forename: Agustina
authors.initials: A
authors.lastname: La-Venia
authors.affiliation: Department of Organic Chemistry, Palacky University771, 46 Olomouc (Czech Republic).
authors.forename: Carlos Alfonso Barea
authors.initials: CA
authors.lastname: Ripoll
authors.affiliation: Farmak, Na vlčinci 16/3, Klášterní Hradisko, 779 00 Olomouc, 251 (Czech Republic).
authors.forename: Ludmila
authors.initials: L
authors.lastname: Hradilová
authors.affiliation: Department of Organic Chemistry, Palacky University771, 46 Olomouc (Czech Republic). vkrchnak@nd.edu.|Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556 (United States). vkrchnak@nd.edu.
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchňák
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D006571:Heterocyclic Compounds
keywords: cyclization; drug discovery; fused-ring systems; regioselectivity; solid-phase synthesis