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Total Synthesis of Lophirone F Hexamethyl Ether
Author(s) -
Le Hoang M.,
Mac Hung D.,
Oh Chang Ho,
Do Dung T.
Publication year - 2019
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.201801827
Subject(s) - chemistry , stereocenter , decarboxylation , stereoselectivity , epimer , cycloaddition , ketone , total synthesis , tetrahydrofuran , ether , yield (engineering) , stereochemistry , aryl , enantioselective synthesis , organic chemistry , solvent , catalysis , alkyl , materials science , metallurgy
A practical and efficient approach for the total synthesis of the (±)‐lophirone F hexamethyl ether was reported. The compound was synthesized in 8 steps with a 14.6 % overall yield. The key features of this synthesis are the stereoselective synthesis of a 2,5‐diaryl‐3,4‐disubstituted tetrahydrofuran skeleton via a sequence of [3+2] cycloaddition/Krapcho decarboxylation and the installation of two aryl ketone groups bypassing potential epimerization of adjacent stereocenters.