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Total Synthesis of Catunaregin and Preliminary Evaluation of Its Antitumor Activity
Author(s) -
Abe Hideki,
Hikichi Takuma,
Emori Kosuke,
Yokosuka Akihito,
Mimaki Yoshihiro,
Kobayashi Toyoharu,
Ito Hisanaka
Publication year - 2018
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.201800219
Subject(s) - chemistry , enantioselective synthesis , total synthesis , aldol reaction , enantiomer , derivative (finance) , stereochemistry , diol , organic chemistry , combinatorial chemistry , catalysis , financial economics , economics
The total synthesis of catunaregin in both racemic and optically active forms was accomplished. The enantioselective synthesis uses the Evans aldol strategy, with an oxazolidinone or thiazolidinethione as the chiral auxiliary. The key features include a syn ‐selective aldol reaction to form the Evans‐ syn or non‐Evans‐ syn product, and a successive ketalization reaction of a furanyl diol derivative under acidic conditions. The biological properties of the synthetic racemate and both enantiomers were evaluated against A549 and HL‐60 human cancer cells.