Stereoselective Total Synthesis of Formosanol, Tsugacetal, and Methyl β-Conidendral
Meiqi Li1, Yiming Liu1, Huiyu Si2
1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Frontiers Science Center for Transformative Molecules, and School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, P. R. China.
Abstract:
The first enantioselective total synthesis of aryltetralin lignan acetals, (-)-formosanol, (+)-tsugacetal, (+)-methyl β-conidendral, and their enantiomers have been accomplished on the basis of the Pd-catalyzed asymmetric allylic cycloaddition as a key step. Six stereoisomers of the lignan acetals have been synthesized via a 7-8 step sequence in up to 14% overall yield. The in vitro cytotoxicity against several cancer cells has preliminarily been examined for the obtained six stereoisomers of lignan acetals.
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