A Stereoselective Synthesis of (+)-Piscidic Acid and Cimicifugic Acid L

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Abstract

Alkylation of the lithium enolate of (2S,3S,5S,6S)-dimethoxy-2,3-dimethyl-1,4-dioxane-5,6-dithiocarboxylate using 4-benzyloxybenzyl bromide stereoselectively gave two new stereogenic centres with the carboxylate groups in a cis relationship. Hydrolytic deprotection of this intermediate produced the natural product (+)-piscidic acid. Installation of a cinnamic acid ester at the secondary hydroxy group was followed by selective deprotection to give a mixture of cis/trans cinnamates in a 3:1 ratio. Finally, the natural product cimicifugic acid L was obtained.

Original languageEnglish
Pages (from-to)7529-7533
Number of pages5
JournalEuropean Journal of Organic Chemistry
Volume2015
Issue number34
DOIs
Publication statusPublished - 1 Dec 2015

Keywords

  • Alkylation
  • Asymmetric synthesis
  • Chiral pool
  • Natural products
  • Total synthesis

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