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Solid‐Phase Synthesis of Tetramic Acid via Resin‐Bound Enol Ethers as a Privileged Scaffold in Drug Discovery
Author(s) -
Schütznerová Eva,
Oliver Allen G.,
Přibylka Adam,
Krchňák Viktor
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800645
Subject(s) - chemistry , solid phase synthesis , wittig reaction , combinatorial chemistry , enol , scaffold , drug discovery , organic chemistry , phase (matter) , catalysis , biochemistry , medicine , peptide , biomedical engineering
This paper reports the practical synthesis of a tetramic acid scaffold on solid phase using simple, commercially available building blocks under mild conditions. Acyclic precursors were assembled on solid phase in four steps, and cyclization was achieved by Wittig olefination. The target compounds contained three points of diversification and allowed for further modifications while still being attached to the resin. Solid‐phase synthesis represents a method of choice, particularly for parallel synthesis, because the intermediates can be isolated simply and quickly by washing the resin beads, which typically takes only minutes.