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Facile Formation of Methylenebis(chalcone)s through Unprecedented Methylenation Reaction. Application to Antiparasitic and Natural Product Synthesis
Author(s) -
Thévenin Marion,
Mouray Elisabeth,
Grellier Philippe,
Dubois Joëlle
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201400104
Subject(s) - chalcone , chemistry , benzophenone , acetophenone , natural product , antiparasitic , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , medicine , pathology
The formation of methylenebis(chalcone)s has been discovered during deprotection with methoxymethyl groups from trihydroxychalcones. Studies on this methylenation reaction led to a mechanism hypothesis that was extended to other chalcones and to dihydrochalcone, acetophenone, benzophenone and flavone derivatives. This new method was applied to the rapid synthesis of natural product piperanduncin C. These original methylenebis compounds were also evaluated for their antiparasitic activity.