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Tandem Thio‐Michael Addition/Remote Lactone Activation of 5‐Hydroxymethylfurfural‐Derived δ‐Lactone‐Fused Cyclopentenones
Author(s) -
A. Gomes Rafael F.,
Ravasco Joao M. J. M.,
Andrade Késsia H. S.,
Coelho Jaime A. S.,
Moreira Rui,
Oliveira Rafael,
Nogueira Fátima,
Afonso Carlos A. M.
Publication year - 2022
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.202102204
Subject(s) - lactone , chemistry , tandem , nucleophile , synthon , combinatorial chemistry , biorefinery , organic chemistry , materials science , composite material , catalysis , raw material
The creation of structurally diverse chemical entities from fairly simple biorefinery products remains a challenge. In this work 5‐hydroxymethylfurfural (HMF) was identified as a key synthon for preparing highly complex cyclopentenones (CP) via tandem 1,4‐addition/elimination/remote lactone activation to external O‐ and N‐nucleophiles in δ‐lactone‐fused‐CPs hotspots. This scaffold was also reactive enough to be incorporated into model cysteine‐peptides in low concentrations, paving the way to a potential translation generating complexity in the synthesis of small peptides. The new enones also exhibited activity against intraerythrocytic Plasmodium falciparum (IC 50 =1.32 μ m ).