Work

Synthesis of Nature‐Inspired Medium‐Sized Fused Heterocycles from Amino Acids

Year: 2015

Type: article

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.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.201501746

Authors: Pilar Ventosa‐Andrés, Agustina La‐Venia, Carlos Alfonso Barea Ripoll, Ludmila Hradilová, Viktor Krchňák

Institutions: Palacký University Olomouc, Farmak (Czechia), University of Notre Dame

Language: English

Topic: Chemical Synthesis and Analysis

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: bronze

Funders: Grantová Agentura České Republiky, European Social Fund

Awards: Solid-phase synthesis of diversely constrained peptidomimetics., G6461011143, G7449853313