Total synthesis of (S)-espicufolin and absolute structure determinaton of espicufolin

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Hidemitsu Uno, Katsuji Sakamoto, Erina Honda and Noboru Ono


Abstract

(S)-Espicufolin was synthesized from 1,4-dimethoxybenzene in 16 steps via an intramolecular acyl-transfer reaction as the key step; the absolute stereochemistry at the 14-position of natural espicufolin was determined to be R.


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