Stereoselective Total Synthesis of Formosanol, Tsugacetal, and Methyl β-Conidendral

  • Org Lett. 2022 Oct 28;24(42):7812-7816. doi: 10.1021/acs.orglett.2c03159.
Meiqi Li  1 ,  Yiming Liu  1 ,  Huiyu Si  2 ,  Xin Zhou  2 ,  Yong Jian Zhang  1  3
Affiliations
  • 1. Shanghai 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.
  • 2. Department of Chemistry, College of Chemistry and Chemical Engineering, Qingdao University, Qingdao 266071, P. R. China.
  • 3. Key Laboratory of Natural Medicines of the Changbai Mountain, Ministry of Education, Yanbian University, Yanji 133002, P. R. China.
PMID: 36222500 DOI: 10.1021/acs.orglett.2c03159
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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