Synthesis of Nature-Inspired Medium-Sized Fused Heterocycles from Amino Acids
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- cyclization, drug discovery, fused-ring systems, regioselectivity, solid-phase synthesis,
- MeSH
- Amino Acids chemical synthesis chemistry MeSH
- Cyclization MeSH
- Heterocyclic Compounds chemical synthesis chemistry MeSH
- Molecular Structure MeSH
- Stereoisomerism MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Amino Acids MeSH
- Heterocyclic Compounds MeSH
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.
Department of Organic Chemistry Palacky University771 46 Olomouc
Farmak Na vlčinci 16 3 Klášterní Hradisko 779 00 Olomouc 251
References provided by Crossref.org
Traceless Solid-Phase Synthesis of [6,7,8 + 5,6,7]-Fused Molecular Frameworks
